Sodium Chloride → 6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-ol

HRID 256230

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[Br:11][CH:12]1[CH:16]2[O:17][C:18](=[O:21])[CH:19]3[CH2:20][CH:13]1[CH2:14][CH:15]23.[K].[Na].[Cl-].[Na+]>C1(C)C=CC=CC=1>[Br:11][CH:12]1[CH:16]2[O:17][CH:18]([OH:21])[CH:19]3[CH2:20][CH:13]1[CH2:14][CH:15]23

Participants

Conditions

Temperature: -60 °C

Procedure

275 ml of a toluene solution of 1.2M of diisobutyl aluminium hydride were slowly added at -60° C. to a mixture of 62.16 g of 6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-one [prepared by method of Ver Nooy et al, J.A.C.S., Vol. 77 (1955), p. 3583] and 500 ml of toluene and the mixture was stirred at -60° C. for 45 minutes and was then poured into aqueous 1M sodium potassium double tartrate. The mixture was stirred for 2 hours and the decanted aqueous phase was saturated with sodium chloride and extracted with methylene chloride. The combined organic phases were evaporated to dryness under reduced pressure to obtain 64.7 g of racemic 6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-ol melting at 104° C.

Workup

stirringThe mixture was stirred for 2 hours
extractionextracted with methylene chloride
customThe combined organic phases were evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-224054a31a66430e9a4abad27f4d8b51
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04701542

Linked notes

Loading…