Sodium Bicarbonate → Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate

HRID 1913784노트

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HRID 1913784 반응식
[C:1]([CH:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(O)=[O:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH:4]([CH2:1][OH:2])[CH2:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)=[CH:23][CH:22]=1)#[N:25]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 57831382Methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate

생성물 1

HCID 57831369Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-5 °C

실험 절차

47.43 ml (47.43 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 8 g (23.71 mmol) of methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate from Example 47A in 200 ml of THF at −10° C. After the mixture has warmed to −5° C. it is stirred at this temperature for 4 h. After the reaction is complete, the reaction mixture is mixed with saturated sodium bicarbonate solution and the solvent is evaporated to dryness. The residue is taken up in dichloromethane, dried over sodium sulphate and, after filtration, again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10). 5.8 g (98% purity, 74% of theory) of a colourless solid are obtained.

후처리

  1. customthe solvent is evaporated to dryness
  2. dry with materialdried over sodium sulphate
  3. filtrationafter filtration
  4. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10)
  5. custom5.8 g (98% purity, 74% of theory) of a colourless solid are obtained

출처 및 근거

ORD 기록
ord-e85cf9f462104ced98911a8a24e5c065
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609727B2

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