Triethylamine → HCID 66755629, compound

HRID 1642000Notes

Reaction equation

HRID 1642000 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:13][CH:14]=[CH2:15].C(N(CC)CC)C.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>ClCCl.C(OCC)(=O)C>[Si:23]([O:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:13][CH:14]=[CH2:15])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 54253994HCID 54253994, compound

Product 1

HCID 66755629HCID 66755629, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-hydroxy-3-allyl-5-methylbenzoate (157 mg, 0.762 mmol) in dichloromethane (5 mL) was treated with triethylamine (0.21 mL, 2 equivalents) and tert-butyldimethylsilyl chloride (172 mg, 1.5 equivalents). The reaction was stirred at room temperature under a nitrogen atmosphere for 3 days by which time TLC analysis showed complete conversion. The reaction was diluted with ethyl acetate (30 mL) and washed with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate. It was then dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to afford the product as a brown oil. Yield=0.239 g (98%).

Workup

  1. washwashed with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate
  2. dry with materialIt was then dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5f550eec4b4b468fac948bc4a5364dd7
Source dataset
uspto-grants-2012_02
Patent number
US08119422B2

Reaction notes

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