Dichloromethane → HCID 59504506, compound

HRID 418904Notes

Reaction equation

HRID 418904 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][O:12][CH2:11][CH:10]2[OH:14])[CH:6]=[CH:7][CH:8]=1.[Cr](Cl)(O)(=O)=O.N1C=CC=CC=1.ClCCl>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][O:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 66652122HCID 66652122, compoundHCID 178526118HCID 178526118, compound

Product 1

HCID 59504506HCID 59504506, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 4-(3-methoxy-phenyl)-tetrahydro-furan-3-ol (10.58 g, 54.0 mmol), pyridine chlorochromate (35.22 g, 163.0 mmol), silica gel (35.0 g), and dichloromethane (200 mL), stir at room temperature. After 3 hours, add ether and filter off the silica gel through a plug of Silica using 50% ethyl acetate/hexanes eluent. Concentrate and flash chromatograph with 10% to 40% ethyl acetate/hexanes to yield the titled compound (5.74 g, 55%) as a clear oil. TLC Rf=0.23 in 3:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.30 (m, 1H), 6.85 (m, 3H), 4.68 (t, 1H, J=9.0 Hz), 4.31 (t, 1H, J=8.8 Hz), 4.19 (d, 1H, J=17.2 Hz), 4.08 (d, 1H, J=17.2 Hz), 3.84 (s, 3H), 3.70 (t, 1H, J=8.1 Hz).

Workup

  1. filtrationfilter off the silica gel through a plug of Silica using 50% ethyl acetate/hexanes eluent
  2. concentrationConcentrate

Sources & evidence

ORD record
ord-e83c551bddf947558996886055423443
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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