Diethyl Ether → HCID 11361671, compound

HRID 1703198Notes

Reaction equation

HRID 1703198 reaction equation
COCCOC[O:7][C@@H:8]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:10]([C@@H:11]([O:35]COCCOC)[CH2:12][C@@H:13]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:34])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[CH2:9]1.CCOCC>C(Cl)Cl.CO.[Br-].[Zn+2].[Br-]>[OH:7][C@@H:8]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:10]([C@@H:11]([OH:35])[CH2:12][C@@H:13]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:34])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH3:25])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:23])[CH3:24])[CH2:9]1

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 22821658HCID 22821658, compound

Product 1

HCID 11361671HCID 11361671, compound

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2.0 g of 3α,6α-bis(β-methoxyethoxymethoxy)-5β-cholest-24-ene, prepared according to Example V, was dissolved in a mixture of 20 ml of methylene chloride and 0.30 ml of methanol, and the solution was stirred with 5 g of zinc bromide for 18 hours. Then, ether was added, the mixture washed with water, the organic layer dried, the solvent evaporated, the residue washed with petroleum ether and dried. From nmr and ir data, the residue was identified as 3α,6α-dihydroxy-5β-cholest-24-ene, the same product as obtained by the acid hydrolysis of the 2-THP, t-Bu, Me3Si and Me2 t-BuSi ethers in Examples VI-IX.

Workup

  1. washthe mixture washed with water
  2. customthe organic layer dried
  3. customthe solvent evaporated
  4. washthe residue washed with petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-1389a13a295c49c8a4b7eb5785507e36
Source dataset
uspto-grants-1982_09
Patent number
US04351767

Reaction notes

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