Dodecanoyl chloride → 4-Dodecoyloxymethyl-3-phenyl-2-triethylsilylfuran

HRID 326372

Reaction equation

HRID 326372 reaction equation
[C:1]1([C:7]2[C:11]([CH2:12][OH:13])=[CH:10][O:9][C:8]=2[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>O1CCCC1>[C:28]([O:13][CH2:12][C:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:8]([Si:14]([CH2:17][CH3:18])([CH2:19][CH3:20])[CH2:15][CH3:16])[O:9][CH:10]=1)(=[O:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 150371503-Phenyl-2-triethylsilyl-4-furanmethanol

Product 1

HCID 150371514-Dodecoyloxymethyl-3-phenyl-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-phenyl-2-triethylsilyl-4-furanmethanol (345 mg, 1.20 mmol) and triethylamine (182 mg, 1.80 mmol) in tetrahydrofuran (15 ml) at 0 degrees under argon was added lauroyl chloride (786 mg, 3.60 mmol). This solution was allowed to warm gradually to room temperature. After stirring an additional 2 hours the white precipitate was filtered off. The filtrate was taken up into ethyl ether, washed with saturated ammonium chloride, saturated sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 2% ethyl ether/hexanes to give the title compound.

Workup

  1. filtrationwas filtered off
  2. washwashed with saturated ammonium chloride, saturated sodium bicarbonate, H2O and brine
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil which
  6. customwas purified by flash chromatography on silica using 2% ethyl ether/hexanes

Sources & evidence

ORD record
ord-e319edf6999c4c0b9e0d6b27c6e90b99
Source dataset
uspto-grants-1993_12
Patent number
US05268387

Linked notes

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