Methanol → HCID 131710578, compound

HRID 1973741Notes

Reaction equation

HRID 1973741 reaction equation
[CH:1](OCC)=[O:2].[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][C@@H:13]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:15]([CH2:16][CH2:17][C@@H:18]3[C@@H:29]2[C:28](=[O:34])[CH2:27][C@@:26]2([CH3:35])[C@H:19]3[CH2:20][CH2:21][C@@H:22]2[C:23](=[O:25])[CH3:24])[CH2:14]1.[H-].[Na+].CO>CS(C)=O>[CH:1]([CH2:24][C:23](=[O:25])[C@@H:22]1[C@:26]2([CH3:35])[C@H:19]([C@H:18]3[C@H:29]([C:28](=[O:34])[CH2:27]2)[C@:30]2([CH3:33])[C@H:15]([CH2:14][C@H:13]([O:12][CH:7]4[CH2:8][CH2:9][CH2:10][CH2:11][O:6]4)[CH2:32][CH2:31]2)[CH2:16][CH2:17]3)[CH2:20][CH2:21]1)=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 131710577HCID 131710577, compound

Product 1

HCID 131710578HCID 131710578, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl formate (0.7 ml) was added to a mixture of 3α-(tetrahydropyran-2ξ-yloxy)-5α-pregnane-11,20-dione (840 mg) and sodium hydride (130 mg) in dry dimethyl sulphoxide (15 ml). The mixture was stirred, under nitrogen for 11/4 hrs., then treated with methyl alcohol to destroy excess sodium hydride, and poured into dilute hydrochloric acid. The precipitate was collected, washed and dried to give title compound (943 mg).

Workup

  1. customto destroy excess sodium hydride
  2. additionpoured into dilute hydrochloric acid
  3. customThe precipitate was collected
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-18f9621415254ea0bc93bd81d2c3ff99
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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