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

HRID 273964

反応式

HRID 273964 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5aad9fb9ddf14a009e581a5cf11bf4b3
出典データセット
uspto-grants-1995_02
特許番号
US05387606

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