Tetrahydrofuran → HCID 70545855, compound

HRID 1703197Notes

Reaction equation

HRID 1703197 reaction equation
[CH3:1][Si:2]([CH3:41])([C:37]([CH3:40])([CH3:39])[CH3:38])[O:3][C@@H:4]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:6]([C@@H:7]([O:29][Si:30]([CH3:36])([CH3:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:8][C@@H:9]3[C@@H:23]2[CH2:22]C[C@@]2(C)[C@H]3CC[C@@H]2[C@H](C)C=CC=O)[CH2:5]1.O1[CH2:46][CH2:45][CH2:44][CH2:43]1>>[CH3:36][Si:30]([CH3:35])([C:31]([CH3:33])([CH3:34])[CH3:32])[O:29][C@@H:7]1[CH2:8][CH2:9][C@@:23]2([CH3:22])[C@H:5]([C@@H:4]([O:3][Si:2]([CH3:41])([CH3:1])[C:37]([CH3:38])([CH3:40])[CH3:39])[CH2:26][C@@H:25]3[C@@H:24]2[CH2:27][CH2:25][C@@:26]2([CH3:4])[C@H:43]3[CH2:44][CH2:45][C@@H:46]2[C@H:23]([CH3:22])[CH2:9][CH2:8][CH:7]=[C:6]([CH3:24])[CH3:5])[CH2:6]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86738580HCID 86738580, compound

Product 1

HCID 70545855HCID 70545855, compound

Procedure

1.4 g of 3α,6α-bis(dimethyl-t-butylsilyloxy)-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 (as described in Example I). The reaction mixture was stirred, refluxed and processed in the manner of Example I. The product remaining after the evaporation of the petroleum ether extract was identified by IR and NMR data as the 3α,6α-bis (dimethyl-t-butylsilyloxy)-5β-cholest-24-ene.

Workup

  1. additionadded dropwise to the ylid solution (as described in Example I)
  2. temperaturerefluxed
  3. customafter the evaporation of the petroleum ether
  4. extractionextract

Sources & evidence

ORD record
ord-7bcffc168ef44e31b1eca9fa3a782e78
Source dataset
uspto-grants-1982_09
Patent number
US04351767

Reaction notes

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