Vinyl Acetate → HCID 22034509, compound

HRID 1792241Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].C12(O)CC3CC(CC(O)(C3)C1)C2.C(OC=C)(=O)C.[CH:25]([O:27][C:28]12[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][C:30]([O:38]C=C)([CH2:31]3)[CH2:29]1)[CH2:35]2)=[CH2:26]>C1(C)C=CC=CC=1>[CH:25]([O:27][C:28]12[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][C:30]([OH:38])([CH2:31]3)[CH2:29]1)[CH2:35]2)=[CH2:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (6.7 mg, 0.01 mmol) and sodium carbonate (64 mg, 0.6 mmol) in toluene (1.0 ml), 1,3-adamantanediol (1 mmol) and vinyl acetate (6 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 5 hours. The reaction mixture was analyzed by gas chromatography to find that 1,3-bis(vinyloxy)adamantane and 3-vinyloxy-1-adamantanol were produced in yields of 41% and 16%, respectively, with a conversion from 1,3-adamantanediol of 97%.

Workup

additionwere added

Sources & evidence

ORD record: ord-c6dfb5bc8847406e9ee7580fa7097c57
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074970B2

Reaction notes

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