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

HRID 326372

반응식

HRID 326372 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e319edf6999c4c0b9e0d6b27c6e90b99
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05268387

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