Triphenylphosphine → Chroman-7-ol

HRID 131158Notes

Reaction equation

HRID 131158 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:12].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[O:12]1[C:6]2[C:5](=[CH:10][CH:9]=[C:8]([OH:11])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 129584034-(3-Hydroxypropyl)benzene-1,3-diol

Product 1

HCID 12236542Chroman-7-olYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(3-Hydroxy-propyl)-benzene-1,3-diol (3.05 g, 18.1 mmol, from Step 1) in anhydrous THF (50 mL ) were added Ph3P (7.13 g, 27.2 mmol, 1.5 eq) and ADDP (6.86 g, 27.2 mmol, 1.5 eq ) under argon. The mixture was stirred at rt for 17 h. The white solid was filtered off and the solvent was removed from the filtrate. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid (1.80 g, 60.5%). 1H-NMR (CD3CN) δ 6.87 (d, 1H), 6.70 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.2 Hz, 1H), 6.20 (d, 1H), 4.12 (t, 2H), 2.69 (t, 2H), 1.95 (m, 2H).

Workup

  1. filtrationThe white solid was filtered off
  2. customthe solvent was removed from the filtrate
  3. customThe residue was purified on silica gel (flash column chromatography)
  4. washeluting with 5% ethyl acetate-hexane

Sources & evidence

ORD record
ord-e754183c2b0548268128ce771017074e
Source dataset
uspto-grants-2008_06
Patent number
US07384947B2

Reaction notes

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