1,6-Hexanediol → Cholest-5-en-3beta-yl 6-hydroxyhexyl ether

HRID 1906579Notes

Reaction equation

HRID 1906579 reaction equation
CC1C=CC(S(O[CH:12]2[CH2:25][C:24]3[C:15]([CH3:38])([CH:16]4[CH:21]([CH2:22][CH:23]=3)[CH:20]3[CH2:26][CH2:27][CH:28]([CH:29]([CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH3:30])[C:19]3([CH3:37])[CH2:18][CH2:17]4)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[CH2:39]([OH:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][OH:45].O1CCOCC1>CCCCCC>[OH:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:46][C@H:12]1[CH2:13][CH2:14][C@@:15]2([CH3:38])[C:24](=[CH:23][CH2:22][C@@H:21]3[C@@H:16]2[CH2:17][CH2:18][C@@:19]2([CH3:37])[C@H:20]3[CH2:26][CH2:27][C@@H:28]2[C@H:29]([CH3:30])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:35])[CH3:36])[CH2:25]1

Participants

5

Reactant 3

HCID 123741,6-HexanediolHCID 312751,4-DioxaneHCID 280698Cholest-5-en-3-yl 4-methylbenzenesulfonate

Product 1

HCID 13799769Cholest-5-en-3beta-yl 6-hydroxyhexyl etherYield 52%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

By use of the procedure described in the literature [Kosower, E. M. and Weinstein, S., J. Am. Chem. Soc., 78 (1956) 4347-4354; and Davis, M., J. Chem. Soc., (1962) 178-181] cholesteryl p-toluenesulfonate and 1,6-hexanediol were condensed in boiling dioxane to give cholest-5-en-3β-yl 6-hydroxyhexyl ether in 52% yield as colorless plates (from hexane), m.p. 75.9°-81° C.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-acd596d75854434dbf0daed186e1118d
Source dataset
uspto-grants-1987_03
Patent number
US04652637

Reaction notes

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