(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone → Dibenzyl ether

HRID 439900Notes

Reaction equation

C([O:8][CH2:9][C@@H:10]1[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C:11]1=[O:23])C1C=CC=CC=1.[CH2:24]([Al](CC(C)C)CC(C)C)C(C)C>C1(C)C=CC=CC=1>[OH:23][CH:11]1[CH2:12][CH:13]([CH2:14][OH:15])[CH:10]1[CH2:9][OH:8].[CH2:16]([O:15][CH2:14][C:13]1[CH:10]=[CH:9][CH:24]=[CH:11][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of (2S-trans) -2,3-bis [(benzyloxy) -methyl]cyclobutanone (0.2 g., 0.645 mmole) in toluene (4 ml.) was added dropwise over 10 minutes to a solution of triisobutylaluminum (0.91M in hexane, 0.9 ml., 0.816 mmole) in toluene (2 ml. ) at -40° C. The mixture was stirred at -50° C. for 4 hours and at -40° C for one hour. A solution of triisobutylaluminum (1 ml., 0.91 mmole) was added to the reaction mixture. After stirring for 30 minutes the reaction was quenched by adding 10% hydrochloric acid (2 ml.) at -40° C. The organic phase was washed with brine, dried (magnesium sulfate), and the solvent was evaporated to give [1S-(1α, 2β, 3β)]-3-hydroxy-2-cyclobutane-dimethanol, dibenzyl ether; TLC (30% ethyl acetate/hexane) Rf =0.3. The product contained about 5% of the isomeric compound; TLC (30% ethyl acetate/hexane) Rf =0.2.

Workup

stirringAfter stirring for 30 minutes the reaction
customwas quenched
additionby adding 10% hydrochloric acid (2 ml.) at -40° C
washThe organic phase was washed with brine
dry with materialdried (magnesium sulfate)
customthe solvent was evaporated

Sources & evidence

ORD record: ord-92b13eaa27074d64a49cf4900755ab1d
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05516903

Reaction notes

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