Acetic Acid → HCID 22345542, compound

HRID 584150Notes

Reaction equation

C[CH:2]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:37][CH:36]=1)[C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3](=[O:33])[CH2:2][O:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])=[CH:39][CH:40]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of methyl 3-[4-[3-(tert-butyldiphenylsilyloxy)propyl]phenoxy]-1-[4-(tert-butoxycarbonyl)phenoxy]-2-propanone (1.44 g, 2.25 mmol) in tetrahydrofuran (35 ml) was treated at 22° C. with acetic acid (0.8 ml) followed by 5 ml (5 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran. The mixture was then heated at 70° C. for 4 hours. The cooled reaction mixture was then 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, 7:3) gave 0.88 g (97%) of the title material as oil.

Workup

customThe cooled reaction mixture
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, 7:3)

Sources & evidence

ORD record: ord-d7cde3950c32499a9cbaff4a10d8bd3e
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924391B2

Reaction notes

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