Water → tert-Butyl (2E)-3-{4-[cyclohexylidene(4-hydroxyphenyl)methyl]-2-fluorophenyl}prop-2-enoate

HRID 229199Notes

Reaction equation

HRID 229199 reaction equation
[C:1]([O:5][C:6]([CH:8]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]1(=[C:34]([C:44]2[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=2)[C:35]2[CH:42]=[CH:41][C:38](C=O)=[C:37]([F:43])[CH:36]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.O.[CH2:52](Cl)Cl>>[C:28]1(=[C:34]([C:44]2[CH:45]=[CH:46][C:47]([OH:50])=[CH:48][CH:49]=2)[C:35]2[CH:42]=[CH:41][C:38](/[CH:52]=[CH:8]/[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[C:37]([F:43])[CH:36]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 860299754-[Cyclohexylidene(4-hydroxyphenyl)methyl]-2-fluorobenzaldehyde

Product 1

HCID 86613509tert-Butyl (2E)-3-{4-[cyclohexylidene(4-hydroxyphenyl)methyl]-2-fluorophenyl}prop-2-enoateYield 68%

Procedure

A solution of (tert-butoxycarbonylmethylene)triphenylphosphorane (610 mg, 1.62 mmol) in CH2Cl2 (10 mL) was added dropwise to 89 (200 mg, 0.644 mmol) dissolved in CH2Cl2 (10 mL) at RT. After stirring for 2 h at RT, water (50 mL) was added and the mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with brine (50 mL) and dried over MgSO4. Concentration followed by flash chromatography (20:1 to 5:1 hexanes:EtOAc) and recrystallization (hexanes:EtOAc) afforded 180 mg (68%) of 90 as a white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 1.52 (s, 9H), 1.59 (br s, 6H), 2.22 (br s, 4H), 5.24 (s, 1H), 6.40 (d, J=16.3 Hz, 1H), 6.76 (d, J=8.4 Hz, 2H), 6.80-6.89 (m, 2H), 6.94 (d, J=8.4 Hz, 2H), 7.37 (t, J=7.9 Hz, 1H), 7.67 (d, J=16.3 Hz, 1H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×25 mL)
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationConcentration
  5. customfollowed by flash chromatography (20:1 to 5:1 hexanes:EtOAc) and recrystallization (hexanes:EtOAc)

Sources & evidence

ORD record
ord-4251a87f4a254206b7586b46fe9cd208
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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