Vinyl Acetate → 5-(Ethenyloxy)tricyclo[3.3.1.1~3,7~]decane-1,3-diol

HRID 916909Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].C12(O)CC3(O)CC(CC(O)(C3)C1)C2.C(OC=C)(=O)C.[CH:26]([O:28][C:29]12[CH2:38][C:33]3([O:39]C=C)[CH2:34][CH:35]([CH2:37][C:31]([O:42]C=C)([CH2:32]3)[CH2:30]1)[CH2:36]2)=[CH2:27].C(OC12CC3CC(OC=C)(CC(O)(C3)C1)C2)=C>C1(C)C=CC=CC=1>[CH:26]([O:28][C:29]12[CH2:30][C:31]3([OH:42])[CH2:37][CH:35]([CH2:34][C:33]([OH:39])([CH2:32]3)[CH2:38]1)[CH2:36]2)=[CH2:27]

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), 1,3,5-adamantanetriol (1 mmol) and vinyl acetate (9 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 1,3,5-tris(vinyloxy)adamantane, 3,5-bis(vinyloxy)-1-adamantanol, and 5-vinyloxy-1,3-adamantanediol were produced in yields of 52%, 18%, and 8%, respectively, with a conversion from 1,3,5-adamantanetriol of 97%.

Workup

additionwere added

Sources & evidence

ORD record: ord-a8aefcb8ba3842608d8c6ec5126b1ed9
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271297B2

Reaction notes

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