[ CAS No. 90843-31-5 ]

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2D
Chemical Structure| 90843-31-5
Chemical Structure| 90843-31-5
Structure of 90843-31-5

Quality Control of [ 90843-31-5 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 90843-31-5 ]

SDS

Product Details of [ 90843-31-5 ]

CAS No. :90843-31-5MDL No. :MFCD00068033
Formula :C10H10O2Boiling Point :308.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :MMVUJVASBDVNGJ-UHFFFAOYSA-N
M.W :162.19Pubchem ID :145220
Synonyms :

Computed Properties of [ 90843-31-5 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 90843-31-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 90843-31-5 ]

  • Downstream synthetic route of [ 90843-31-5 ]

[ 90843-31-5 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 90843-31-5 ]
  • [ 383-63-1 ]
  • (Z)-4-(2,3-Dihydro-benzofuran-5-yl)-1,1,1-trifluoro-4-hydroxy-but-3-en-2-one [ No CAS ]
  • 2
  • [ 90843-31-5 ]
  • [ 454-31-9 ]
  • (Z)-4-(2,3-Dihydro-benzofuran-5-yl)-1,1-difluoro-4-hydroxy-but-3-en-2-one [ No CAS ]
  • 3
  • [ 90843-31-5 ]
  • [ 146321-88-2 ]
YieldReaction ConditionsOperation in experiment
99% With pyridine; hydroxylamine hydrochloride; In methanol; at 20℃; for 16h; W-(2,3-Dihydro-1-benzofuran-5-yl)acetamide (192). NH2OH HCI (7.3 g, 105 mmol) was added to a stirred solution of ketone 191 (14.2 g, 87.7 mmol) and pyridine (9.2 mL, 114 mmol) in MeOH (100 mL) and the mixture stirred at 20 0C for 16 h. The solvent was evaporated and the residue partitioned between brine and EtOAc. The organic fraction was dried and the solvent evaporated to give crude 1-(2,3-dihydro-1-benzofuran-5- yl)ethanone oxime (15.3 g, 99%). HCI gas was bubbled through a solution of the oxime (15.3 g, 86.5 mmol) in Ac2O (16.3 mL, 173 mmol) and HOAc (54 mL, 865 mmol), and the solution stood at 20 0C for 24 h. The precipitate was poured into ice/water, stirred for 2 h, the solid filtered and washed with water and dried. The aqueous fraction was extracted EPO with DCM (2 x 50 ml_), the combined organic extract dried and the solvent evaporated. The slurry was treated with water (20 mL) and evaporated several times to remove Ac2O. The combined solids were purified by chromatography, eluting with a gradient (50-100%) of EtOAc/pet. ether, to give acetamide 192 (7.94 g, 52%) as a white solid: mp 92-93 0C [lit. (Blade-Font, A.; de Mas Rocabayera, T. J. Chem. Soc. P1, 1982, 814-848) mp 93 0C]; 1H NMR delta 7.47 (br s, 1 H, H-4), 7.21 (br s, 1 H, NH), 6.99 (dd, J = 8.5, 2.1 Hz, 1 H, H-6), 6.69 (d, J = 8.5 Hz, 1 H, H-7), 4.55 (t, J = 8.7 Hz, 2 H, H-2), 3.18 (br t, J = 8.7 Hz, 2 H, H- 3), 2.13 (S1 3 H1 CH3).
With pyridine; hydroxylamine hydrochloride; In methanol; at 20℃; Into a 2000 mL round-bottom flask, was placed a solution of [90843-31-5]1-(2,3-dihydrobenzofuran-5-yl)ethanone (67 g, 413.58 mmol, 1.00 equiv) in MeOH (600 mL). To this was added NH2OH.HCl (34.5 g, 496.40 mmol, 1.20 equiv). To the mixture was added pyridine (Py, 42.5 g, 537.97 mmol, 1.30 equiv). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The residue was dissolved in 100 mL of water. The resulting solution was extracted two times with 100 mL of EtOAc and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 70 g (crude) of [90843-31-5]1-(2,3-dihydrobenzofuran-5-yl)ethanone oxime. HCl gas was bubbled through a solution of the oxime (70 g) in Ac2O(86 mL) and HOAc(500 mL). The resulting solution was allowed to react, with stirring, overnight at 20 C. The precipitate was poured into ice/water. The mixture was stirred for 4 h. A filtration was performed. The solid was product (part 1). The filtrate was extracted two times with dichloromethane and was dried over Na2SO4 and concentrated. The solid was also product (part 2). Two parts combined and this resulted in 70 g(86%) N-(2,3-dihydrobenzofuran-5-yl)acetamide as a brown oil.
  • 4
  • [ 496-16-2 ]
  • [ 108-24-7 ]
  • [ 90843-31-5 ]
YieldReaction ConditionsOperation in experiment
91% With trifluoroacetic acid; at 20℃; for 1.5h; General procedure: An oven-dried vial was charged with anisole 1a (0.75 mmol, 1.0 equiv), acetic anhydride 2a (1.5 mmol, 2.0 equiv) and TFA (0.8 mL). The reaction mixture was stirred at room temperature and monitored by TLC or GC-MS. The reaction typically took 1.5 h to complete. Upon completion, aqueous sodium hydrogen carbonate was added and the aqueous phase was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography to afford ketone product 3a. Alternatively, the product can also be obtained without workup: upon completion, the solvent was removed under reduced pressure and the residue was subjected to silica gel flash column chromatography.
With zinc(II) chloride; at 95 - 105℃; for 10h; A mixture of 44.4 g (0.37 moles) of 2,3-dihydrobenzofuran and 37.8 g (0.37 moles) of acetic anhydride were added with 5.0 g (37 mmoles) of anhydrous zinc chloride. The mixture was heated to 95-105 0C for 10 hrs; after cooling to room temperature the mixture is added with 50 ml of water and 50 ml of dichloromethane. The organic phase was separated and the aqueous phase was extracted twice with dichloromethane (2x 30 ml). The organic phases were collected together, and washed with 50 ml of a saturated aqueous solution of sodium carbonate. The organic phase was separated and evaporated u.v. (20 C/21 mbar). The residue was then distilled at 99-100 C/0.08 mbar obtaining 14.5 g (0.089 moles) of 5-acetyl-2,3- dihydrobenzofuran. 1H NMR (400 MHz; CDCI3): delta: 2.50 (s, 3H); 3.20 (t, 2H, J = 8.7 Hz); 4.64 (t, 2H, J = 8.7 Hz); 6.76 (d, 1 H, J = 8.4 Hz); 7.76 (m, 1 H); 7.81 (m, 1 H).13C-NMR (CDCI3, 100MHz): delta: 26.22; 28.79; 72.02; 108.72; 125.34; 127.50; 130.17; 130.48; 164.19; 196.41.
With zinc(II) chloride; at 95 - 105℃; for 10h; A mixture of 44.4 g (0.37 moles) of 2,3-dihydrobenzofuran and 37.8 g (0.37 moles) of acetic anhydride were added with 5.0 g (37 mmoles) of anhydrous zinc chloride. The mixture was heated to 95-105 C for 10 hrs; after cooling to room temperature the mixture is added with 50 ml of water and 50 ml of dichloromethane. The organic phase was separated and the aqueous phase was extracted twice with dichloromethane (2x 30 ml). The organic phases were collected together, and washed with 50 ml of a saturated aqueous solution of sodium carbonate. The organic phase was separated and evaporated u.v. (20 C/21 mbar). The residue was then distilled at 99-100 C/0.08 mbar obtaining 14.5 g (0.089 moles) of 5-acetyl-2,3-dihydrobenzofuran. 1H NMR (400 MHz; CDCl3): delta: 2.50 (s, 3H); 3.20 (t, 2H, J = 8.7 Hz); 4.64 (t, 2H, J = 8.7 Hz); 6.76 (d, 1H, J = 8.4 Hz); 7.76 (m, 1H); 7.81 (m, 1H). 13C-NMR (CDCl3, 100MHz): delta: 26.22; 28.79; 72.02; 108.72; 125.34; 127.50; 130.17; 130.48; 164.19; 196.41.
  • 5
  • [ 90843-31-5 ]
  • [ 22065-85-6 ]
  • 3-(1-benzyl-piperidin-4-yl)-1-(2,3-dihydro-benzofuran-5-yl)-3-hydroxy-propan-1-one [ No CAS ]
  • 6
  • [ 496-16-2 ]
  • [ 75-36-5 ]
  • [ 90843-31-5 ]
  • 5,7-diacetyl-2,3-dihydro-benzofuran [ No CAS ]
  • 7
  • [ 496-16-2 ]
  • [ 75-36-5 ]
  • [ 90843-31-5 ]
YieldReaction ConditionsOperation in experiment
99% aluminum (III) chloride; In dichloromethane; at -10℃; for 0.5h; Example 5; Preparation of 5-(2,3-dihydrobenzofuran-5-yl)-3-(3-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)benzyl)-5-methylimidazolidine-2,4-dione; 5-a) Preparation of 5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione; 2,3-Dihydrobenzofuran (10 g, 83.2 mmol) was dissolved in dichloromethane (400 mL). The resultant mixture was added sequentially with acetyl chloride (11.8 mL, 167 mmol) and aluminum chloride (33.3 g, 250 mmol) at -10 C., and stirred at -10 C. for 0.5 hour. The reaction solution was added with 5% aqueous solution of hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. 1-(2,3-Dihydrobenzofuran-5-yl)ethanone (13.4 g, yield 99%) was obtained as a colorless oil.1H-NMR (CDCl3) delta: 2.55 (3H, s), 3.25 (2H, t, J=8.6 Hz), 4.67 (2H, t, J=8.6 Hz), 6.80 (1H, d, J=8.1 Hz), 7.80 (1H, dd, J=1.9, 8.1 Hz), 7.85 (1H, d, J=1.9 Hz).
99% With aluminum (III) chloride; In dichloromethane; at -10℃; for 0.5h; a) Preparation of 5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione 2,3-Dihydrobenzofuran (10 g, 83.2 mmol) was dissolved in dichloromethane (400 mL), added sequentially with acetyl chloride (11.8 mL, 167 mmol) and alminium chloride (33.3 g, 250 mmol) at -10 C., and the mixture was stirred at -10 C. for 0.5 hours. The reaction solution was added 5% aqueous solution of hydrochloric acid, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. 1-(2,3-Dihydrobenzofuran-5-yl)ethanone (13.4 g (yield 99%)) was obtained as a colorless oil. 1H-NMR (CDCl3) delta: 2.55 (3H, s), 3.25 (2H, t, J=8.6 Hz), 4.67 (2H, t, J=8.6 Hz), 6.80 (1H, d, J=8.1 Hz), 7.80 (1H, dd, j=1.9, 8.1 Hz), 7.85 (1H, d, J=1.9 Hz).
97% With aluminum (III) chloride; In dichloromethane; at -10℃; for 3h; To a solution of 2,3-dihydrobenzofuran (1 g, 8.3mmol) in DCM (10mL) was added acetyl chloride (1.3g, 16.6mmol) and AICI3 (3.3g, 24.6mmol) slowly at -10C. The reaction mixture was stirred at -10C for 3h. The TLC showed the reaction to be complete. The reaction mixture was diluted with 5% aqueous HCI (10ml_) and extracted with DCM (3x1 OmL). The combined organic layers were washed with saturated aqueous bicarbonate solution (100ml_), brine (100ml_), dried (Na2S04), filtered and concentrated under reduced pressure to afford 1-(2,3- dihydrobenzofuran-5-yl)ethan-1-one as a brown liquid. Yield: 1.34g (97%); MS (ESI+) for CHNOS m/z 163.0[M+H]+; 1 H NMR (400 MHz, CDCI3): <5 7.86 (s, 1 H), 7.79 (d, J = 8.4Hz, 1 H), 6.80 (d, J = 8.4 Hz, 1 H), 4.66 (t, J = 8.8 Hz, 2H), 3.25 (t, J = 8.8 Hz, 2H), 2.52 (s, 3H).
94% Preparation of [90843-31-5]1-(2,3-dihydrobenzofuran-5-yl)ethanone Into a 500 mL 3-necked round-bottom flask, was placed a solution of acetyl chloride (62 g) in dry dichloromethane (400 mL). To this was added aluminum(III) chloride (55.6 g, 1.00 equiv). The mixture was allowed to react, with stirring, for 30 min at -10 C. (solution A). Into another 2000 nm 3-necked round-bottom flask, was placed a solution of 2,3-dihydrobenzofuran (50 g, 0.42 mmol, 1.00 equiv) in dry dichloromethane (500 mL) at -10 C. The solution A was added to the above via a cannula, and was stirred for 30 min at 0 C. The mixture was poured into ice/HCl (5:1 v/v, 1 L). The resulting solution was allowed to react, with stirring, for an additional 2 h while the temperature was maintained at room temperature. The resulting solution was extracted three times with 500 mL of CH2Cl2 and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a 1:100 EtOAc/PE solvent system. This resulted in 67 g (94%) of [90843-31-5]1-(2,3-dihydrobenzofuran-5-yl)ethanone as a yellow solid.
94% Preparation of [90843-31-5]1-(2,3-dihydrobenzofuran-5-yl)ethanone Into a 500 mL 3-necked round-bottom flask, was placed a solution of acetyl chloride (62 g) in dry dichloromethane (400 mL). To this was added aluminum(III) chloride (55.6 g, 1.00 equiv). The mixture was allowed to react, with stirring, for 30 min at -10 C. (solution A). Into another 2000 mL 3-necked round-bottom flask, was placed a solution of 2,3-dibydrobenzofuran (50 g, 0.42 mmol, 1.00 equiv) in dry dichloromethane (500 mL) at -10 C. The solution A was added to the above via a cannula, and was stirred for 30 min at 0 C. The mixture was poured into ice/HCl(5:1 v/v, 1 L). The resulting solution was allowed to react, with stirring, for an additional 2 h while the temperature was maintained at room temperature. The resulting solution was extracted three times with 500 mL of CH2Cl2 and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a 1:100 EtOAc/PE solvent system. This resulted in 67 g (94%) of [90843-31-5]1-(2,3-dihydrobenzofuran-5-yl)ethanone as a yellow solid.
61% With aluminum (III) chloride; In dichloromethane; at -10 - -6℃; for 0.5h; EXAMPLE 1(S)-2-{1-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-pyrrolidin-3-yl}-2,2-diphenyl-acetamide 1-(2,3-Dihydrobenzofuran-5-yl)ethanone: At about -10 C., a solution of acetyl chloride (12.40 g, 158.13 mmol) dissolved in dichloromethane (10 mL) was added to a solution of 2,3-dihydrobenzofuran (10.0 g, 83.22 mmol) dissolved in dichloromethane. Maintaining the temperature below -6 C., aluminum chloride (11.0 g, 83.22 mmol) was added, and the mixture was then stirred for an about 30 minutes. At about -10 C., 2 N hydrochloric acid (85 mL) was added and the mixture was extracted with dichloromethane. The organic extract was concentrated, and the solid residue was recrystallized from hexane to yield the title product as a white solid (8.1 g, 61%). m.p. 63-66 C.; 1H NMR (400 MHz, CDCl3) delta 2.55 (s, 3H), 3.26 (t, J=8.9 Hz, 2H), 4.67 (t, J=8.7 Hz, 2H), 6.81 (d, J=8.3 Hz, 1H), 7.80 (d, J=8.3 Hz, 1H), 7.86 (s, 1H); IR (KBr) upsilon 2983, 2918, 1659, 1599, 1486, 1431, 1354, 1282, 1237 cm-1; MS 163 (M+1).

  • 10
  • [ 90843-31-5 ]
  • 2-(2,3-dihydrobenzofuran-5-yl)-1H-indole [ No CAS ]
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