Water → HCID 59305304, compound

HRID 2240958Notes

Reaction equation

HRID 2240958 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:18]3[CH2:21][C:20](=[O:22])[CH2:19]3)[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1.[BH4-].[Na+].O>CO>[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:18]3[CH2:21][CH:20]([OH:22])[CH2:19]3)[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59305321HCID 59305321, compound

Product 1

HCID 59305304HCID 59305304, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[3-(4-Difluoromethoxy-phenylethynyl)-phenyl]-cyclobutanone (0.834 g, 2.67 mmol) was dissolved in methanol (100 ml) and chilled in an ice bath. After 20 minutes sodium borohydride (0.159 gm, 4.02 mmol) was added and stirring was continued for another 20 minutes. Water (2 ml) was added and stirring was continued for another 20 minutes The reaction was concentrated by rotary evaporation and partitioned between water and dichloromethane. The organic layer was dried with magnesium sulfate and concentrated to an oil 845 mg (quant); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.92 (m, 2H) 2.47-2.64 (m, 2H) 2.68-2.91 (m, 1H) 3.87-4.09 (m, 1H) 5.03 (d, J=7.4 Hz, 1H) 7.03 (d, J=2.6 Hz, 1H) 7.18 (d, J=8.8 Hz, 2H) 7.21-7.25 (m, 1H) 7.27-7.32 (m, 2H) 7.38 (s, 1H) 7.58 (d, J=8.8 Hz, 2H).

Workup

  1. temperaturechilled in an ice bath
  2. stirringstirring
  3. waitwas continued for another 20 minutes
  4. concentrationThe reaction was concentrated by rotary evaporation
  5. custompartitioned between water and dichloromethane
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. concentrationconcentrated to an oil 845 mg (quant)

Sources & evidence

ORD record
ord-90b85572b146469bad60560906c93fdf
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

Loading…