Triethylamine → HCID 54529210, compound

HRID 247891Notes

Reaction equation

HRID 247891 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].C(N(CC)CC)C.[C:22]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[Si:26]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 141214-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 54529210HCID 54529210, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (100 mL) solution of 1-(4'-hydroxy-3'-methoxyphenyl)-1-butene-3-one (10.0 g, 52 mmol) is added triethyl amine (5.8 g, 57.2 mmol) and t-butylchlorodimethyl silane (15.7 g, 104 mmol). The reaction is stirred at room temperature for 12 hours under an argon atmosphere. The mixture is washed with water (3×100 mL) and brine (100 mL). The organic layer is dried over MgSO4 and evaporated. Flash chromatography (ethyl ether/hexane 1:1) affords 12.8 g (80%) of the desired 1-(4'-t-butyldimethylsilyloxy-3'-methoxyphenyl)-1-butene-3-one, mp=65°-68° C.

Workup

  1. washThe mixture is washed with water (3×100 mL) and brine (100 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-9b54f7bddead4d4aa5b16fd475188053
Source dataset
uspto-grants-1993_05
Patent number
US05208251

Reaction notes

Loading…