Pivalic acid → HCID 131719271, compound

HRID 1781551Notes

Reaction equation

[Si:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]([C:21]2[CH2:25][CH2:24][CH2:23][CH:22]=2)O)=[C:16]([O:26][CH3:27])[C:15]([CH3:28])=[C:14]2[C:10]=1[C:11](=[O:29])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30]([OH:36])(=[O:35])[C:31](C)(C)C.[CH2:37](C(CC)(CC)C([O-])([O-])[O-])[CH3:38]>C(OCC)(=O)C>[Si:1]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:21]2/[CH:22]([CH2:31][C:30]([O:36][CH2:37][CH3:38])=[O:35])[CH2:23][CH2:24][CH2:25]/2)=[C:16]([O:26][CH3:27])[C:15]([CH3:28])=[C:14]2[C:10]=1[C:11](=[O:29])[O:12][CH2:13]2)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-[2-(4-tert-butyldimethylsilyloxy-1,3-dihydro -6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-1-hydroxyeth-1-yl]cyclopent-1-ene (0.22 g) in triethylorthoacetate (10 ml) was treated with pivalic acid (0.010 g) and then heated to 100° C., and maintained at that temperature for 18 hours. After cooling to ambient temperature, the solution was diluted with 1:1 ethyl acetate:hexanes and washed sequentially with water, saturated aqueous sodium bicarbonate, and brine. Drying over magnesium sulfate was followed by evaporation; chromatography of the residue on silica gel (10% ethyl acetate in hexanes) afforded ethyl (E) 2-[2-[2-[4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-isobenzofuran-5-yl]ethylidene]-cyclopent-1-yl]acetate (0.11 g) as an oil.

Workup

temperaturemaintained at that temperature for 18 hours
temperatureAfter cooling to ambient temperature
washhexanes and washed sequentially with water, saturated aqueous sodium bicarbonate, and brine
dry with materialDrying over magnesium sulfate
customwas followed by evaporation

Sources & evidence

ORD record: ord-0b6617e9cfd7449aaea81f512395c478
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05633279

Reaction notes

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