Ethyl Acetate → HCID 68998580, compound

HRID 1661523Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]23[C@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][C:13](=O)[C@@:12]2(O)[C:11]2[C:24]([O:31][CH2:32][CH3:33])=[CH:25]C(OCC)=C[C:10]=2[O:9]3)=[CH:4][CH:3]=1.CO[C:36](=[O:38])[O-:37].CO[Mg+].[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]23[C@H:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C@H:14]([C:36]([OH:37])=[O:38])[CH2:13][C@@H:12]2[C:43]2[C:42]([O:45][CH2:46][CH3:47])([OH:44])[CH2:25][C:24]([O:31][CH2:32][CH3:33])=[CH:11][C:10]=2[O:9]3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 500 mg (1.08 mmol) of (3S*,3aR*,8bR*)-3a-(4-chlorophenyl)-6,8-diethoxy-8b-hydroxy-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1-one (Example 15A) and 1.08 ml (2.15 mmol) of a 2 M solution of methoxymagnesium methyl carbonate in DMF is heated with stirring at 100° C. in a closed vessel for 16 h. The resulting suspension is then poured into a mixture of ice-cold 5 N hydrochloric acid and ethyl acetate. The organic phase is separated off, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered with suction and concentrated. 531 mg of crude product are employed directly in the next stage without further characterization.

Workup

temperatureis heated
customThe organic phase is separated off
washwashed with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
filtrationfiltered with suction
concentrationconcentrated

Sources & evidence

ORD record: ord-c9e4a6358c964ec8a9e3705d4a08f25f
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030347B2

Reaction notes

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