Acetic Anhydride → HCID 22850339, compound

HRID 1974780Notes

Reaction equation

HRID 1974780 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].O[CH:9]1[C:16](=C)C[C@H:14]2[C@@H:10]1[CH2:11][C@@H:12]([O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1)[C@H:13]2/[CH:18]=[CH:19]/[C@@H:20]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>>[C:5]([O:4][CH:1]1[C:9](=[CH2:16])[CH2:10][C@H:14]2[C@@H:2]1[CH2:11][C@@H:12]([O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1)[C@H:13]2/[CH:18]=[CH:19]/[C@@H:20]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 22850341HCID 22850341, compound

Product 1

HCID 22850339HCID 22850339, compoundYield 97%

Procedure

Acetic anhydride (5.0 ml) and pyrdine (5.0 g) were added to the (1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-(2-tetrahydropyranyloxy)-1-octenyl]-7-(2-tetrahydropyranyloxy)bicyclo[3.3.0]octane (928 mg, 2.00 mmoles) obtained in Example 65, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and subjected to column chromatography (silica gel 200 g; hexane/ethyl acetate=19/1) to give (1S,2RS,5S,6S,7R)-2-acetoxy-3-methylene-6-[(E,3S)-3-(2-tetrahydropyranyloxy)-1-octenyl]-7-(2-tetrahydropyranyloxy)bicyclo[3.3.0]octane (982 mg, 1.94 mmoles, 97%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f30feb678e84439fb57e1f1c3a4eacae
Source dataset
uspto-grants-1994_02
Patent number
US05283349

Reaction notes

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