Triphenylphosphine → HCID 58002971, compound

HRID 1516683Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[CH:13]=C[O:15][C:11]=2[CH:10]=[C:9]2[C:4]=1[C:5](=[O:18])[CH2:6][C:7]([CH3:17])([CH3:16])[O:8]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:38]=[O+][O-]>ClCCl>[OH:15][C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:18])[CH2:6][C:7]([CH3:17])([CH3:16])[O:8]2)=[C:3]([O:2][CH3:1])[C:12]=1[CH:13]=[O:38]

Participants

Conditions

Temperature: -78 °C

Procedure

500 mg (2.03 mmol) of 4-methoxy-7,7-dimethyl-6,7-dihydro-5H-furo[3,2-g]chromen-5-one (Example 1A) and 666 mg (2.54 mmol) of triphenylphosphine are initially charged, and 50 ml of dichloromethane are added. The mixture is cooled to −78° C., and ozone is then introduced for about 5 min. Once the color of the solution has turned to blue, excess ozone is flushed out with oxygen. The solution is stirred for another two hours and slowly warmed to room temperature. The mixture is concentrated and the residue that remains is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 5:1) This gives 370 mg (72% of theory) of the title compound.

Workup

customis flushed out with oxygen
temperatureslowly warmed to room temperature
concentrationThe mixture is concentrated
customthe residue that remains is purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 5:1) This gives 370 mg (72% of theory) of the title compound

Sources & evidence

ORD record: ord-f87f56c65d524524b48d253bc32f9a57
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227511B2

Reaction notes

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