[ CAS No. 89048-25-9 ] {[proInfo.proName]}

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Quality Control of [ 89048-25-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89048-25-9 ]

CAS No. :	89048-25-9	MDL No. :	MFCD09835388
Formula :	C₁₂H₁₆O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	240.25	Pubchem ID :	-
Synonyms :

Safety of [ 89048-25-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 89048-25-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 89048-25-9 ]

[ 89048-25-9 ] Synthesis Path-Downstream 1~7

1
[ 4885-02-3 ]
[ 35896-58-3 ]
[ 89048-25-9 ]

Yield	Reaction Conditions	Operation in experiment
90%		To a stirred solution of 5a (4.24 g, 20 mmol) in CH2Cl2 (30 mL) was added dichloromethyl methyl ether (6.89 g, 60 mmol) at 0 C followed by addition of TiCl4 (11.38 g, 60 mmol)41 S. Ohkawa, S. Terao, Z. Terashit, Y. Shibouta and K. Nishikawa, J. Med. Chem. 34 (1991), p. 267. Full Text via CrossRef \| View Record in Scopus \| Cited By in Scopus (36)41 (see Scheme 4). The resulting mixture was stirred for 4 h at ambient temperature and then poured into ice water. After stirring vigorously for 10 min, the organic layer was separated. It was washed with water, dried, and evaporated. The residue was chromatographed on silica gel to give 5b (90%) as a light yellow liquid. 1H NMR (500.0 MHz, CDCl3, 298 K): 3.99 (s, 12H, 4× -OCH3), 2.25 (s, 3H, -CH3), 10.45 (s, H, -CHO) ppm.
83%	With titanium tetrachloride; In dichloromethane; at 0 - 20℃; for 4h;	A mixture of <strong>[35896-58-3]2,3,4,5-<strong>[35896-58-3]tetramethoxytoluene</strong></strong> (2.12 g, 10 mmol) and 1,1-dichlorodimethyl ether (1.8 mL, 20 mmol) in DCM (200 mL) was stirred at room temperature (rt), then the solution was allowed to cool to 0 oC and was added titanium tetrachloride (2.18 mL, 20 mmol). The mixture was allowed to warm to rt and stirred for 4 hours. The ice water was added slowly to quench the reaction and extracted with DCM, washed with brine and dried over Na2SO4, filtered and evaporated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (EtOAc / petroleum ether = 1 / 20) to yield the target products (2 g, 83%) as colorless oil. 1H NMR (400 MHz, CDCl3) delta 10.43 (s, 1H), 4.02 (s, 3H), 3.94 (s, 3H), 3.91 (s, 3H), 3.76 (s, 3H), 2.46 (s, 3H). MS (ESI): m/z 241.1 [M+H]+.

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 267 - 276
[2]Journal of the American Chemical Society,2012,vol. 134,p. 20681 - 20689
[3]Tetrahedron,2011,vol. 67,p. 5990 - 6000
[4]Journal of the American Chemical Society,2011,vol. 133,p. 12366 - 12369
[5]Bioorganic Chemistry,2019,vol. 89
[6]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1125 - 1129
[7]Journal of Medicinal Chemistry,2010,vol. 53,p. 1200 - 1210

2
[ 31575-75-4 ]
[ 89048-25-9 ]
1-(3, 4,5, 6-Tetramethoxy-2-methylphenyl)-1-(2-benzyloxyphenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With magnesium In tetrahydrofuran at 0℃; for 2h;	6 1-(3.4.5.6-Tetramethoxy-2-methylphenyl-1-1-2-benzyloxyphenyl)methanol REFERENCE EXAMPLE 6 1-(3.4.5.6-Tetramethoxy-2-methylphenyl-1-1-2-benzyloxyphenyl)methanol Under ice-cooling, into a Grignard reagent (35 ml, a tetrahydrofuran solution) prepared from 2-(benzyloxy)bromobenzene (11.50 g, 0.044 mol) and magnesium (1.16 g, 0.048 mol) was dropped a solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (5.00 g, 0.021 mol) in anhydrous tetrahydrofuran (30 ml) and the mixture was stirred for 2 hours more. The reaction solution was poured into a saturated aqueous solution of ammonium chloride followed by extracting with ether. The extract was washed with a saturated saline and dried. The reaction solution was filtered and the crude product obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (8.80 g, 0.021 mol. 99%).
	With ammonium chloride; magnesium In tetrahydrofuran	R.6 1-(3, 4,5, 6-Tetramethoxy-2-methylphenyl)-1-(2-benzyloxyphenyl)methanol Reference Example 6 1-(3, 4,5, 6-Tetramethoxy-2-methylphenyl)-1-(2-benzyloxyphenyl)methanol An anhydrous tetrahydrofuran (30 ml) solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (5.00 g, 0.021 mol) was added dropwise under ice cooling to a Grignard reagent (35 ml tetrahydrofuran solution) prepared from 2-(benzyloxy)bromobenzene (11.50 g, 0.044 mol) and magnesium (1.16 g, 0.048 mol), and the resulting solution was stirred for 2 hours. The reaction solution was poured in an aqueous solution of saturated ammonium chloride and extracted with ether. The extract was washed with saturated brine and then dried. The reaction solution was filtered, the filtrate was concentrated and the obtained crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 4:1) to obtain the titled compound (8.80 g, 0.021 mol, 99%).

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2004/39061, 2004, A1 Location in patent: Page/Page column 10
[2]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1314712, 2003, A1

3
[ 6793-92-6 ]
[ 89048-25-9 ]
[ 464215-98-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With magnesium In tetrahydrofuran at 0℃; for 2h;	5 1-[3,4,5,6-Tetramethoxy-2-methylphenyl-1-(4-benzoy]oxyphenyl)methanol REFERENCE EXAMPLE 5 1-[3,4,5,6-Tetramethoxy-2-methylphenyl-1-(4-benzoy]oxyphenyl)methanol Under ice-cooling, into a Grignard reagent (30 ml, a tetrahydrofuran solution) prepared from 4-(benzyloxy)bromobenzene (8.00 g, 0.030 mol) and magnesium (0.81 g, 0.033 mol) was dropped a solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (3.65 g, 0.015 mol) in anhydrous tetrahydrofuran (20 ml) and the mixture was stirred for 2 hours more. The reaction solution was poured into a saturated aqueous solution of ammonium chloride followed by extracting with ether. The extract was washed with a saturated saline and dried. The reaction solution was filtered and the crude product obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (5.93 g, 0.014 mol, 92%).

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2004/39061, 2004, A1 Location in patent: Page/Page column 10

4
[ 53087-13-1 ]
[ 89048-25-9 ]
1-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(3-benzyloxyphenyl)-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With magnesium; In tetrahydrofuran; at 0℃; for 2h;	REFERENCE EXAMPLE 4 1-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-3-benzyloxyyhenyl]methanol Under ice-cooling, into a Grignard reagent (150 ml, a tetrahydrofuran solution) prepared from 3-(benzyloxy)bromobenzene (18.4 g, 0.070 mol) and magnesium (1.87 g, 0.077 mol) was dropped a solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (14 g, 0.058 mol) in anhydrous tetrahydrofuran (50 ml) and the mixture was stirred for 2 hours more. The reaction solution was poured into a saturated aqueous solution of ammonium chloride followed by extracting with ether. The extract was washed with a saturated saline and dried. The reaction solution was filtered and the crude product obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (23.5 g, 0.055 mol, 95percent).
	With ammonium chloride; magnesium; In tetrahydrofuran;	Reference Example 4 1-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(3- benzyloxyphenyl) methanol An anhydrous tetrahydrofuran (50 ml) solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (14 g, 0.058 mol) was added dropwise under ice cooling to a Grignard reagent (150 ml tetrahydrofuran solution) prepared from 3-(benzyloxy)bromobenzene (18.4 g, 0.070 mol) and magnesium (1.87 g, 0.077 mol), and the resulting solution was stirred for 2 hours. The reaction solution was poured in an aqueous solution of saturated ammonium chloride and extracted with ether. The extract was washed with saturated brine and then dried. The reaction solution was filtered, the filtrate was concentrated and the obtained crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 4:1) to obtain the titled compound (23.5 g, 0.055 mol, 95percent).

Reference： [1]Patent: US2004/39061,2004,A1 .Location in patent: Page/Page column 10
[2]Patent: EP1314712,2003,A1

5
[ 79286-79-6 ]
[ 89048-25-9 ]
N,N'-bis(2,3,4,5-tetramethoxy-6-methylbenzyl)-3-aminopyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hydroxide; sodium borohydrid; In methanol;	PREPARATION EXAMPLE 20 N,N'-bis(2,3,4,5-tetramethoxy-6-methylbenzyl)-<strong>[79286-79-6]3-aminopyrrolidine</strong> STR65 To a solution of 2,3,4,5-tetramethoxy-6-methylbenzaldehyde (12.7 g, 52.9 mmol) in methanol (100 ml) was added <strong>[79286-79-6]3-aminopyrrolidine</strong> (2.0 g, 23.2 mmol) and the mixture was stirred under reflux-heating for 4 hours. After cooling the mixture to room temperature, sodium borohydride (2.0 g, 52.6 mmol) was added by portions and the mixture was stirred for 3 hours. After 5(w/v)% aqueous solution of sodium hydroxide was added to the reaction solution which was then extracted with ethyl acetate. The organic layer was washed with successive water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and a silica gel column chromatography of the residue gave 6.34 g of the title compound from the fraction of methanol/chloroform (1/19) eluent. Yield=51%

Reference： [1]Patent: US5756475,1998,A

6
[ 35896-58-3 ]
[ 89048-25-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hexamethylenetetramine; In water; trifluoroacetic acid;	PREPARATION EXAMPLE 28 2,3,4,5-tetramethoxy-6-methylbenzaldehyde STR73 To a solution of <strong>[35896-58-3]1,2,3,4-tetramethoxy-5-methylbenzene</strong> (34.3 g, 162 mmol) in trifluoroacetic acid (200 ml) was added hexamethylenetetramine (25.0 g, 178 mmol), and the solution was heated under reflux for 3 hours. The solvent was distilled off under reduced pressure. Water (200 ml) was added to the residue which was then heated under reflux for one hour, neutralized with 3N sodium hydroxide and extracted with ethyl acetate (200 ml*3), and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography to give 34.9 g of the title compound. Yield=90% 1 H NMR (CDCl3) d 2.46 (s, 3H), 3.76 (s, 3H), 3.91 (s, 3H), 3.95 (s, 3H), 10.43 (s, 1H)

Reference： [1]Patent: US5756475,1998,A
[2]Journal of Chemical Research,2014,vol. 38,p. 408 - 409
[3]Chemical Papers,2015,vol. 69,p. 486 - 489
[4]Research on Chemical Intermediates,2015,vol. 41,p. 6393 - 6396

7
[ 10602-01-4 ]
[ 89048-25-9 ]
2-{4-[hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]phenyl}-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium In tetrahydrofuran	1.1 Step 1. Step 1. 2-{4-[hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]phenyl}-1,3-dioxolane To an ice-cold solution of 2,3,4,5-tetramethoxy-6-methylbenzaldehyde (5.03 g, 20.94 mmol) in THF (200 ml) was added dropwise a Grignard reagent prepared from 2-(4-bromophenyl)-1,3-dioxolane (12.0 g, 52.4 mmol) and magnesium (1.40 g, 57.6 mmol), and then stirred at room temperature for 4 hours. The reaction mixture was poured into water and was extracted with ether. After the extract was washed with water and dried, and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (hexane: ethyl acetate = 3: 1) to yield the title compound (7.80 g, 20.0 mmol, yield 96%).

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1008346, 2000, A1

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[ CAS No. 89048-25-9 ] {[proInfo.proName]}

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[ 89048-25-9 ] Synthesis Path-Downstream 1~7

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