3-(1-Hydroxytridecyl)-5-trimethylsilylfuran → HCID 19909501, 화합물

HRID 1534343노트

반응식

HRID 1534343 반응식
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]

참가 물질

6

반응물 3

HCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 199094994-Iodobutanoyl chlorideHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 19909501HCID 19909501, 화합물

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5e898d088c3a44d48caaea003925f4d6
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05089485

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