3-(1-Hydroxytridecyl)-5-trimethylsilylfuran → HCID 19909501、化合物

HRID 1534343ノート

反応式

HRID 1534343 の反応式
C([Li])(C)(C)C.[OH:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[I:29][CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34]>CCCCC.O1CCCC1>[I:29][CH2:30][CH2:31][CH2:32][C:33]([O:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:34]

参加物

6

反応物 3

HCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 199094994-Iodobutanoyl chlorideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 19909501HCID 19909501、化合物

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

tert-Butyl lithium (a 1.7 M solution in pentane; 0.33 ml, 0.56 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (188.1 mg, 0.56 mmol) in tetrahydrofuran (4 ml) at 0° under argon. After 15 minutes, a solution of 4-iodobutyryl chloride (129 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued overnight while the cooling bath attained room temperature. The mixture was quenched with water and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts afforded an oil, which was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a colorless oil.

後処理

  1. waitwas continued overnight while the cooling bath attained room temperature
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulphate)
  6. customextracts afforded an oil, which
  7. customwas purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane)

出典と根拠

ORDレコード
ord-5e898d088c3a44d48caaea003925f4d6
出典データセット
uspto-grants-1992_02
特許番号
US05089485

反応ノート

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