Triphenylphosphine → HCID 67966896, compound

HRID 527594Notes

Reaction equation

HRID 527594 reaction equation
O[CH2:2][C:3]1([CH3:17])[CH2:5][CH:4]1[C:6]1[C:11]([O:12][CH2:13][O:14][CH3:15])=[CH:10][CH:9]=[CH:8][C:7]=1[OH:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:2][C:3]12[CH2:5][CH:4]1[C:6]1[C:11]([O:12][CH2:13][O:14][CH3:15])=[CH:10][CH:9]=[CH:8][C:7]=1[O:16][CH2:17]2

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 67958076HCID 67958076, compound2×

Product 1

HCID 67966896HCID 67966896, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-(hydroxymethyl)-2-methylcyclopropyl]-3-{[(methyloxy)methyl]oxy}phenol (Intermediate 123, 307 mg) in dry tetrahydrofuran (10 ml) were added triphenylphosphine (338 mg, 1.288 mmol) and bis(1-methylethyl)(E)-1,2-diazenedicarboxylate (261 mg, 1.288 mmol). The reaction turned yellow and was stirred for 20 minutes at room temperature under nitrogen. The solvent was then evaporated under vacuum to give the crude product as pale yellow oil. The residue obtained was purified by silica gel chromatography (Companion system, with a gradient from pure Cyclohexane to cyclohexane/ethyl acetate 10/1) to give the title compound as a white solid (280 mg).

Workup

  1. customThe solvent was then evaporated under vacuum
  2. customto give the crude product as pale yellow oil
  3. customThe residue obtained
  4. customwas purified by silica gel chromatography (Companion system

Sources & evidence

ORD record
ord-4bbcd25fe46c480c9b891d482a698c8c
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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