Water → HCID 54500622, compound

HRID 479306Notes

Reaction equation

HRID 479306 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)CC)C.O>C(Cl)Cl>[CH3:3][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][CH:19]=[CH:18][CH2:17]4)=[CH:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

5

Reactant 3

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

Product 1

HCID 54500622HCID 54500622, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

The title compound was prepared by using a method analogous to a method described in J Chemical Research (miniprint) (1979) 4714-4755. 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 and was then slowly heated to the room temperature. The reaction mixture was added 15 ml 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 A giving cholesta-2,8,14-triene, 0.23 g. Melting point: 104.7° C. Elementary analysis: Cal C: 88.45; H: 11.55. Found C: 88.58; H: 11.89. NMR: Hd: 5.64 (m 2H; C2—H; C3—H)d 5.35 (s,1H C 15H). Cd: 125.95 (C3), 125.67 (C2).

Workup

  1. temperaturewas then slowly heated to the 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

Sources & evidence

ORD record
ord-a31c490cfd394679a3e0a2d2f45f414a
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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