Triethylamine → Methyl 4-tert-butyldimethylsilyloxy-3,5-di(2-propen-1-yl)benzoate

HRID 1741741Notes

Reaction equation

HRID 1741741 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:15][CH:16]=[CH2:17].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[Si:18]([O:1][C:2]1[C:3]([CH2:15][CH:16]=[CH2:17])=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[CH2:12][CH:13]=[CH2:14])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 193856193,5-Diallyl-4-hydroxybenzoic acid methyl ester

Product 1

HCID 19385712Methyl 4-tert-butyldimethylsilyloxy-3,5-di(2-propen-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The product of Step B (3.1 g, 13.36 mmol) was treated with tert-butyldimethylsilyl chloride (2.22 g, 1.1 equiv), triethylamine (3 mL) and DMAP (0.1 equiv) in dichloromethane overnight. The mixture was concentrated and flash chromatographed with 5% and then 10% ethyl acetate in hexane to finish 4.5 g (97%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customflash chromatographed with 5%

Sources & evidence

ORD record
ord-fe5818e7ec7844a8859e2f49b76f66cd
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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