HCID 67924099, compound → HCID 67924091, compound

HRID 1493662Notes

Reaction equation

HRID 1493662 reaction equation
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@:16]4([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:18]=[CH:17]4)[CH2:11]1)(=O)C1C=CC=CC=1>C1COCC1.C(O)C.[O-]CC.[Na+]>[C:38]([CH2:37][C@:16]12[C:15]3[CH2:14][CH2:13][C@@H:12]4[C@:32]([CH3:35])([CH2:33][CH2:34][C@H:10]([OH:9])[CH2:11]4)[C:31]=3[CH2:30][CH2:29][C@:28]1([CH3:36])[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:18]=[CH:17]2)([O:40][CH2:41][CH3:42])=[O:39]

Participants

5

Reactant 1

HCID 67924099HCID 67924099, compound

Product 1

HCID 67924091HCID 67924091, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 2723922Sodium ethoxideSolvent

Procedure

A solution of 3β-benzoyloxy-14α-carbethoxymethyl-5α-cholest-8,15-diene (2.06 g, 3.58 mmole) in THF (90 mL), absolute ethanol (40 mL) and 20% ethanolic sodium ethoxide (5 mL) was heated at 75° C. for one hour. The reaction was partitioned between ethyl ether and iced dilute HCl. The organic layer was washed with water, dried and concentrated to yield the crude 14α-carbethoxymethyl-5α-cholest-8,15-dien-3β-ol. This was dissolved in ethyl acetate (150 mL) and platinum oxide (1 g) was added. The mixture was agitated under an atmosphere of hydrogen for 2 hours. The catalyst was filtered and the concentrated filtrate was flash chromatographed with 2:1 to 1:1 hexane in ethyl acetate to yield 1.59 g of 14α-carbethyoxymethyl-5α-cholest-8-en-3β-ol; mp 72°-73° C. (from CH3CN).

Workup

  1. customThe reaction was partitioned between ethyl ether and iced dilute HCl
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6c0cb49581241008bb0f11ade43cf77
Source dataset
uspto-grants-1991_06
Patent number
US05023250

Reaction notes

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