Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Triphenylphosphine Oxide

HRID 2419621Notes

Reaction equation

HRID 2419621 reaction equation
[OH:1][C@@H]1CC[C@@]2(C)C(CC[C@@H]3[C@@H]2C[C@H](O)[C@@]2(C)[C@H]3CC[C@@H]2[C@H](C)CCC=O)C1.C(C=[P:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(OC)=O>C1C=CC=CC=1>[C:46]1([P:33](=[O:1])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 53909052HCID 53909052, compound

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 64.8 g of (0.149) of 3α,12α-dihydroxy-24-cholanal, diformate and 55 g (10% excess) of carbomethoxymethylene triphenylphosphorane 12 in 250 ml of dry benzene was refluxed for 6 hr. The solvent was then removed under reduced pressure and the residue treated with 400 ml of a 3:1 solution of hexane-ether. The resulting precipitate was filtered to give 39 g of crude triphenylphosphine oxide. The filtrate was concentrated, dissolved in a minimum of benzene and washed through 600 g of silica gel with a 2% ethyl acetate-benzene solution. The solvent was removed and the residue crystallized from hexane to give 49 g of 5-(3α,12α-diformyloxy-5β-pregnane-20-yl)-trans-2-pentenoic acid methyl ester mp 112°-115°.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additionthe residue treated with 400 ml of a 3:1 solution of hexane-ether
  3. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-336470eaa2084d08bf0a5140c68bed96
Source dataset
uspto-grants-1978_08
Patent number
US04107188

Reaction notes

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