Methanol → HCID 54534405, compound

HRID 479314Notes

Reaction equation

HRID 479314 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@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][C@@H:10]1[OH:29])[CH3:8])[CH3:3].C([O-])(=O)C.[Na+].CO>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[OH:28][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:26]2([CH3:27])[C@H:12]3[CH2:11][C:10](=[O:29])[C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH2:17]1

Participants

7

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 57274845HCID 57274845, compound

Product 1

HCID 54534405HCID 54534405, compoundYield 82.2%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of cholest-5-ene-3β,16β-diol (700 mg, 1.7 mmol) and sodium acetate (trihydrate) 4.6 g, 34 mmol) in glacial acetic acid (85 mL) was added dropwise, a solution of chromium trioxide in water (1.7 mL) and acetic acid (0.8 mL). After stirring for 16 hours, methanol (5mL) was added and the reaction mixture concentrated at reduced pressure. Water was added and the aqueous phase extracted using dichloromethane. Drying over magnesium sulphate, concentration and purification by flash chromatography gave the title compound (560 mg).

Workup

  1. concentrationthe reaction mixture concentrated at reduced pressure
  2. additionWater was added
  3. extractionthe aqueous phase extracted
  4. dry with materialDrying over magnesium sulphate, concentration and purification by flash chromatography

Sources & evidence

ORD record
ord-bbf884e04b7e4770ad22d51ffba6570c
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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