Water → HCID 20599266, compound

HRID 479305Notes

Reaction equation

HRID 479305 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 20599266HCID 20599266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-ea45a2d8ab9f4d318517b0d5785dc763
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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