Tetrahydrofuran → HCID 70544959, compound

HRID 1703196Notes

Reaction equation

HRID 1703196 reaction equation
[C:1]([O:5][C@@H:6]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:8]([C@@H:9]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:10][C@@H:11]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:21])[CH:17]=[CH:18][CH:19]=O)[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].O1C[CH2:39][CH2:38][CH2:37]1>>[C:1]([O:5][C@@H:6]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:8]([C@@H:9]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])[CH2:10][C@@H:11]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:21])[CH2:17][CH2:18][CH:19]=[C:38]([CH3:39])[CH3:37])[CH2:7]1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86738579HCID 86738579, compound

Product 1

HCID 70544959HCID 70544959, compound

Procedure

A solution of 3α,6α-bis(t-butyloxy)-5β-cholen-24-al (prepared as described in my U.S. patent application Ser. No. 236,160) was dissolved in 5 ml of tetrahydrofuran and added dropwise to the ylid solution (described in Example I). The mixture was stirred for 2 hours and then the solution was refluxed for 2 hours. After evaporation of the solvent, the residue was dissolved in a 90% methanol-10% water mixture, extracted with petroleum ether and the petroleum ether extract evaporated. The residue was identified by NMR and IR data as the 3α,6α-bis(t-butyloxy)-5β-cholest-24-ene.

Workup

  1. additionadded dropwise to the ylid solution (described in Example I)
  2. temperaturethe solution was refluxed for 2 hours
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue was dissolved in a 90% methanol-10% water mixture
  5. extractionextracted with petroleum ether
  6. extractionthe petroleum ether extract
  7. customevaporated

Sources & evidence

ORD record
ord-8fc6d6e60a284b079af764c9466da9bf
Source dataset
uspto-grants-1982_09
Patent number
US04351767

Reaction notes

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