Triphenylphosphine → (R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuran

HRID 2280679Notes

Reaction equation

HRID 2280679 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11](O)=[CH:10][C:9]=1[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:6][C@@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[CH:10][C:9]=1[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 819704-Bromo-3,5-dimethylphenolHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 86697120(R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuranYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-Tetrahydrofuran-3-ol 2a (1 g, 11.35 mmol) was dissolved in 30 mL of dichloromethane, followed by addition of 4-bromo-3,5-dimethylphenol (2.28 g, 11.35 mmol). The reaction solution was cooled down to 0° C., followed by addition of triphenylphosphine (3.57 g, 13.62 mmol) and diisopropyl azodicarboxylate (2.75 g, 13.62 mmol) successively. The reaction solution was warmed up to room temperature and stirred for 12 hours. The resulting solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound (R)-3-(4-bromo-3,5-dimethylphenoxy)tetrahydrofuran 35a (2.27 g, yield 73.9%) as a colorless oil.

Workup

  1. temperatureThe reaction solution was warmed up to room temperature
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-602a45a7f9f145a7a017d86b2a968835
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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