(S)-4-benzyloxy-2-(2-benzyloxyethoxy)-1-trityloxybutane → (S)-3-(2-hydroxyethoxy)-4-trityloxybutanol

HRID 1168052Notes

Reaction equation

C([O:8][CH2:9][CH2:10][C@H:11]([O:33][CH2:34][CH2:35][O:36]CC1C=CC=CC=1)[CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:36][CH2:35][CH2:34][O:33][C@H:11]([CH2:12][O:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:10][CH2:9][OH:8]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-4-Benzyloxy-2-(2-benzyloxyethoxy)-1-trityloxy-butane (51 mg, 0.092 mmol) was dissolved in ethyl acetate (3 ml). To the solution was added 5% Pd—C (5.0 mg) and the mixture was stirred under an atmosphere of hydrogen for 15 hours at 50° C. After filtering off catalyst, the filtrate was condensed in vacuo, and the residue was subjected to silica gel chromatography to give (S)-3-(2-hydoxyethoxy)-4-trityloxybutanol (28 mg, yield 78%).

Workup

filtrationAfter filtering off catalyst
customcondensed in vacuo

Sources & evidence

ORD record: ord-6170360ff1ff439fac79fe170033e79e
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620977B1

Reaction notes

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