Water → HCID 20599266, 화합물

HRID 479305노트

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HRID 479305 반응식
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C:12]([C:13]3[CH2:14][CH2:15][CH:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@H:18](O)[CH2:17]4)=[CH:11][CH2:10]1)[CH3:8])[CH3:3].C(N(S(F)(F)[F:35])CC)C.O>C(Cl)Cl>[F:35][C@@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[CH:16]([CH2:15][CH2:14][C:13]3[C:12]4[C@:26]([CH3:27])([CH2:25][CH2:24][C:23]=32)[C@@H:9]([C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:10][CH:11]=4)[CH2:17]1

참가 물질

5

반응물 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 22211628Cholesta-8,14-diene-3-beta-ol

생성물 1

HCID 20599266HCID 20599266, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

Cholesta-8,14-diene-3β-ol (1.17 g, 3 mmol) was dissolved in 10 ml of methylenechloride and cooled to −78° C. Over 10 min a solution of diethylaminosulfur trifluoride (1.4 g, 8.7 mmol) in 10 ml of methylenechloride was added at −78° C. The mixture was stirred for 1½ hour at −78° C. and was then slowly heated to room temperature. To the reaction mixture was added 15 ml of water while stirring was continued. The organic phase was separated and washed with 30 ml of 5% NaHCO3 and then with water. The organic phase was dried with MgSO4 and evaporated to dryness. The residue was purified by column chromatography using heptane for a first fraction and heptane/acetone, 95:5 (w/w) for a second fraction containing 3α-fluorocholesta-8,14 diene, 0.14 g (12%). Melting point: 98.6° C. Elementary analysis: Cal C: 83.88; H: 11.21; F: 4.91. Found C: 83.92; H: 11.75. 19F-NMR: d 181.0 and 181.2 (JHCF 45.2 Hz, C3-aF).

후처리

  1. temperaturewas then slowly heated to room temperature
  2. stirringwhile stirring
  3. customThe organic phase was separated
  4. washwashed with 30 ml of 5% NaHCO3
  5. dry with materialThe organic phase was dried with MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography
  8. additioncontaining 3α-fluorocholesta-8,14 diene, 0.14 g (12%)

출처 및 근거

ORD 기록
ord-ea45a2d8ab9f4d318517b0d5785dc763
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645953B2

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