Water → (E)-3-(3'-adamantan-1-yl-4'-cyanomethoxybiphenyl-4-yl)-acrylic acid methyl ester

HRID 41727Notes

Reaction equation

HRID 41727 reaction equation
Br[CH2:2][C:3]#[N:4].C([O-])([O-])=O.[K+].[K+].[CH3:11][O:12][C:13](=[O:39])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]34[CH2:38][CH:33]5[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]5)[CH2:30]3)[CH2:36]4)[CH:23]=2)=[CH:18][CH:17]=1.O>CN(C=O)C>[CH3:11][O:12][C:13](=[O:39])/[CH:14]=[CH:15]/[C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:2][C:3]#[N:4])=[C:24]([C:29]34[CH2:38][CH:33]5[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]5)[CH2:30]3)[CH2:36]4)[CH:23]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 10293655(E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-acrylic acid methyl ester

Product 1

HCID 67399554(E)-3-(3'-adamantan-1-yl-4'-cyanomethoxybiphenyl-4-yl)-acrylic acid methyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoacetonitrile (84 mg, 0.7 mmol), K2CO3 (166 mg, 1.2 mmol) and KI (53 mg, 0.32 mmol) were added to a solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid methyl ester (250 mg, 0.64 mmol) in DMF (2 ml). The mixture was stirred at RT for 3 h. Cold water was added and the solution was extracted with EtOAc. The organic layer was washed with a saturated solution of NaHCO3, water and brine. The organic layer was dried over Na2SO4 and evaporated under reduced pressure to obtain (E)-3-(3′-adamantan-1-yl-4′-cyanomethoxybiphenyl-4-yl)-acrylic acid methyl ester (240 mg, 88%).

Workup

  1. extractionthe solution was extracted with EtOAc
  2. washThe organic layer was washed with a saturated solution of NaHCO3, water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7cf0c2aac1e54fdeaae89e501bc05fa1
Source dataset
uspto-grants-2013_09
Patent number
US08530517B2

Reaction notes

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