(2,6-Difluorophenyl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-methanone → 4-(Cyclopentylidene(2,6-difluorophenyl)methyl)phenol

HRID 1261387Notes

Reaction equation

HRID 1261387 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17]C2CCCCO2)=[CH:13][CH:12]=1)=O.[CH:24]1([Mg]Br)[CH2:28][CH2:27][CH2:26][CH2:25]1>>[C:24]1(=[C:9]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 57701080(2,6-Difluorophenyl)(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-methanoneHCID 178419650HCID 178419650, compound

Product 1

HCID 577010884-(Cyclopentylidene(2,6-difluorophenyl)methyl)phenol

Procedure

Compound 12 was synthesized from ketone 5 (1 mmol) and cyclopentyl magnesium bromide (2 mmol) using procedure B described for synthesis of 6. The THP protection group was cleaved under the acidic conditions used. Yield: 18 mg (16%). 1H-NMR (400 MHz, CDCl3): δ ppm 7.26-7.14 (m, 1H), 7.13-7.12 (m, 2H), 6.89-6.85 (m, 2H), 6.76-6.73 (m, 2H), 4.75 (s, 1H), 2.50 (broad t, J=6.4 Hz, 2H), 2.13 (broad t, J=6.4 Hz, 2H), 1.75-1.58 (m, 4H).

Workup

  1. customdescribed for synthesis of 6

Sources & evidence

ORD record
ord-3f05ce975b1f4e46aa7907dae03b8b6e
Source dataset
uspto-grants-2013_06
Patent number
US08470872B2

Reaction notes

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