Sulfuric Acid → HCID 86753028, compound

HRID 482212Notes

Reaction equation

HRID 482212 reaction equation
[C:1]([O:4][C@@:5]1([C:28]#[CH:29])[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14]([CH:15]=[C:16]([O:23]CC)[CH2:17][CH2:18]1)=[C:13]([CH:26]=O)[CH2:12]3)(=[O:3])[CH3:2].[BH4-].[Na+].S(=O)(=O)(O)O>C(O)C.CN(C=O)C>[C:1]([O:4][C@@:5]1([C:28]#[CH:29])[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14](=[CH:15][C:16](=[O:23])[CH2:17][CH2:18]1)[C:13](=[CH2:26])[CH2:12]3)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 18664615HCID 18664615, compound

Product 1

HCID 86753028HCID 86753028, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

2.8 g of 17beta-acetoxy 3-ethoxy 17alpha-ethynyl 6-formyl 3,5-estradiene, 8.5 ml (abs) ethanol (3.03 vol), 7 ml dimethylformamide (2.5 vol), and 0.13 g sodium borohydride (0.046 p) are introduced under agitation and under a nitrogen atmosphere into a 50 ml three-necked flask. The reaction is stopped after agitation for 22 hours. The reaction medium is hydrolyzed by introducing a solution composed of 2.8 ml (1 vol) of 2N sulphuric acid, 6 ml (2.1 vol) DMF, and 6 ml (2.1 vol) (abs) ethanol over 10 minutes. 2.1 g (yield=84%) of a creamy white product is obtained. M.p.=157° C.

Workup

  1. customfor 22 hours
  2. additionby introducing a solution

Sources & evidence

ORD record
ord-6caa8df0b2cc4e4ea94541cfb97e9cc0
Source dataset
uspto-grants-1998_08
Patent number
US05795884

Reaction notes

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