Triethylamine → Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate

HRID 1645952Notes

Reaction equation

HRID 1645952 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH:13]=[CH2:14].C(N(CC)CC)C.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23]>ClCCl.CN(C)C1C=CN=CC=1>[Si:26]([O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH:13]=[CH2:14])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 939882Methyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 19385705Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.168 g (26.9 mmol) of the product of Step B in 50 mL of dichloromethane was added 4.40 mL (2.95 mmol) of triethylamine, 4.46 g (2.95 mmol) of tert-butyldimethylchlorosilane, 0.100 g of 4-dimethylaminopyridine, and the reaction mixture was stirred at room temperature for 2 hours. The mixture was then diluted with 50 mL dichloromethane, washed with 100 mL 1N hydrochloric acid, dried (MgSO4), filtered and evaporated. The residual oil (7.993 g, 97%) was used in the next step without further purification.

Workup

  1. washwashed with 100 mL 1N hydrochloric acid
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual oil (7.993 g, 97%) was used in the next step without further purification

Sources & evidence

ORD record
ord-05651672dd964d97b90ae831f14ae6c8
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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