Methanol → HCID 68135350, compound

HRID 267804Notes

Reaction equation

HRID 267804 reaction equation
[C:1]([O:4][C@:5]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](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:6](=[O:9])[CH:7]=[O:8])(=[O:3])[CH3:2].CN1CCCC1=[O:35].CO.[C-]#N.[K+]>[O-2].[Mn+4].[O-2].C(O)(=O)C>[C:1]([O:4][C@:5]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](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:6](=[O:9])[C:7]([OH:35])=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 13387N-methyl-2-pyrrolidoneHCID 86733159HCID 86733159, compound

Product 1

HCID 68135350HCID 68135350, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

4.0 g. of 17α-acetoxy-3,20-dioxo-4-pregnen-21-al is agitated at room temperature for 5 minutes in 100 ml. of N-methylpyrrolidone with 32 ml. of methanol, 6.4 ml. of concentrated acetic acid, 12 g. of manganese(IV) oxide, and 1.4 g. of potassium cyanide. The reaction product is then isolated as set forth in Example 39(b). After recrystallization from acetone-petroleum ether, 1.98 g. of the methyl ester of 17α-acetoxy-3,20-dioxo-4-pregnene-21-oic acid is obtained, m.p. 190.3°.

Workup

  1. customThe reaction product is then isolated
  2. customAfter recrystallization from acetone-petroleum ether, 1.98 g

Sources & evidence

ORD record
ord-7b7f146d4166473bab28fe5478892e69
Source dataset
uspto-grants-1976_03
Patent number
US03944577

Reaction notes

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