HCID 58531369, compound → HCID 11086076, compound

HRID 1889710Notes

Reaction equation

HRID 1889710 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[C:9]=2[O:16][CH3:17])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[O:15])[C:9]=2[O:16][CH3:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 58531369HCID 58531369, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11086076HCID 11086076, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4′-chloro-2-methoxybiphenyl-3-yl)methanol (800 mg, 3.21 mmol, 1.0 eq) in dry DCM at 0° C. was added pyridinium chlorochromate (3.0 g, 3.91 mmol, 4.3 eq). The reaction mixture was stirred for 1 h, filtered on a silica pad and washed with DCM. The filtrate was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel (60-120) eluting with 5-10% ethyl acetate/hexane to afford the desired product (0.430 g, 54%). 1H NMR (400 MHz, CD3OD) δ 3.83-3.94 (s, 3H), 7.02-7.05 (t, 1H), 7.14-7.16 (d, 1H), 7.46-7.48 (t, 1H), 7.57-7.59 (t, 1H), 7.61-7.63 (m, 2H), 7.74-7.76 (d, 1H). MS (ESI): 248.0 (M+H)+.

Workup

  1. filtrationfiltered on a silica pad
  2. washwashed with DCM
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by flash column chromatography on silica gel (60-120)
  5. washeluting with 5-10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b785e1335a3a40d5932490b9371c0092
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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