Sodium hydride → HCID 53775193, 화합물

HRID 322973노트

반응식

HRID 322973 반응식
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].Cl[CH:20]([C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[Cl:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:28]=1[CH:20]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 10657149HCID 10657149, 화합물HCID 54244821HCID 54244821, 화합물

생성물 1

HCID 53775193HCID 53775193, 화합물수율 35.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Hydroxy-4-(3-thienylmethoxy)benzonitrile (0.5 g) is added portionwise to a stirred suspension of sodium hydride (90 mg, 60% dispersion in mineral oil) in dry DMF (100 mL). After stirring at ambient temperature for 30 minutes, ethyl (RS)-4-chloro-4-(2-chloro-6-fluorophenyl)butanoate (0.62 g) is added in one portion and the reaction stirred for 48 hours at 90° C. The reaction mixture is concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v). Fractions homogeneous in the required product are combined and evaporated to give ethyl (RS)-4-(2-chloro-6-fluorophenyl)-4-(2-cyano-5-(3-thienylmethoxy)phenoxy)butanoate (360 mg) as an orange oil.

후처리

  1. stirringthe reaction stirred for 48 hours at 90° C
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:2 v/v)
  8. customevaporated

출처 및 근거

ORD 기록
ord-828e31278bb9460c8fdf3956eb03445d
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211234B1

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