Isopropanol → HCID 57592484, compound

HRID 1784411Notes

Reaction equation

HRID 1784411 reaction equation
Br.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[C:13]([OH:24])=[CH:14][C:15]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17][C:16]=3[CH:23]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:30]=CC=C[CH:26]=1.C(O)(C)C.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.CO.ClCCl>[F:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[C:13]([O:24][CH:25]([CH3:30])[CH3:26])=[CH:14][C:15]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17][C:16]=3[CH:23]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68831940HCID 68831940, compound

Product 1

HCID 57592484HCID 57592484, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

The phenol (D6) (1.1 g), triphenylphosphine (1.7 g) and isopropanol (0.5 ml) were dissolved in tetrahydrofuran and cooled to 0° C., Diisopropyl azodicarboxylate (1.3 ml) was added dropwise and the mixture stirred at room temperature for 1 h. The mixture was passed through an SCX column and then chromatography on silica eluting with 4% methanol/dichloromethane afforded the titled compound D29 (870 mg) MH+ 365

Sources & evidence

ORD record
ord-cab4f33480a74a2e8c8345aa89758166
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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