Acetic Acid → HCID 131725061, compound

HRID 584163Notes

Reaction equation

[Si]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:49]=[CH:48][C:25]([O:26][CH2:27][CH:28]([O:44][C:45](=[O:47])[CH3:46])[CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:49]=[CH:48][C:25]([O:26][CH2:27][CH:28]([O:44][C:45](=[O:47])[CH3:46])[CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of (2R and 2S)-3-[4-[3-(tert-butyldiphenylsilyloxy)propyl]phenoxy]-1-[4-(tert-butoxycarbonyl)phenoxy]-2-acetoxypropane (7.38 g, 10.8 mmol) in tetrahydrofuran (100 ml) was treated with acetic acid (3.7 ml) and 24 ml (24 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and the resulting mixture was heated at 70° C. for 4 hours. The cooled mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate, brine and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 75:25) gave 4.76 g (97%) of the title alcohol as an oil.

Workup

washwashed with water, saturated sodium bicarbonate, brine
dry with materialdried (magnesium sulfate)
customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 75:25)

Sources & evidence

ORD record: ord-1c205eb45f7643038928f24275c04c98
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924391B2

Reaction notes

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