Triphenylphosphine → HCID 86703885, compound

HRID 471445Notes

Reaction equation

HRID 471445 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH3:11][S:12]([C:15]1([CH2:18]O)[CH2:17][CH2:16]1)(=[O:14])=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>O1CCCC1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:18][C:15]2([S:12]([CH3:11])(=[O:14])=[O:13])[CH2:17][CH2:16]2)=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 819704-Bromo-3,5-dimethylphenolHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 575787931427028-11-2

Product 1

HCID 86703885HCID 86703885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-bromo-3,5-dimethylphenol, (306 mg, 1.52 mmol), (1-Methanesulfonyl-cyclopropyl)-methanol (228 mg, 1.52 mmol), and triphenylphosphine (399 mg, 1.52 mmol) are suspended in dry tetrahydrofuran (10 mL) and cooled to 0° C. Di-tert-butylazodicarboxylate (350 mg, 1.52 mmol) is added and the mixture stirred at 50° C. for 48 hours then at room temperature for a further 48 hours. The mixture is concentrated under vacuum then partitioned between water and dichloromethane, The organic phase is dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-20% ethyl acetate in cyclohexane) to give the title compound as a crude material which was used without further purification (Yield 664 mg).

Workup

  1. waitat room temperature for a further 48 hours
  2. concentrationThe mixture is concentrated under vacuum
  3. customthen partitioned between water and dichloromethane
  4. customThe organic phase is dried
  5. customthe solvent removed under vacuum
  6. customThe residue is purified by flash chromatography (0-20% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-39753b914b4b445ab38229b114cac4de
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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