Acetic Acid → HCID 12832925, compound

HRID 1703201Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:41])[CH2:4][C:5](=[O:40])[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:25]C2CCCCO2)[C:18]([CH3:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:32]C2CCCCO2)[CH2:12][C:11]1=[O:39].C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:41])[CH2:4][C:5](=[O:40])[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:25])[C:18]([CH3:23])([CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([OH:32])[CH2:12][C:11]1=[O:39]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 42 mg of the tetrahydropyran-2-yloxy compound (prepared as described in Example 2), 0.4 ml of 65% v/v aqueous acetic acid, and 4 drops of tetrahydrofuran was stirred for 5 minutes at 80° C. The reaction solution was diluted with ethyl acetate, washed successively with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulphate, and concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to obtain 12.6 mg of the title compound having the following physical characteristics:

Workup

washwashed successively with water
dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified by column chromatography on silica gel using
additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record: ord-cbadc33c859047e0981fb815e29f175c
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04351846

Reaction notes

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