Bicarbonate Ion → Methyl 4-(7-cyano-3-hydroxymethylheptyl)benzoate

HRID 1927425노트

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HRID 1927425 반응식
[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[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-]>C1COCC1>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH:4]([CH2:1][OH:2])[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)#[N:22]

참가 물질

4

반응물 2

HCID 769Bicarbonate IonHCID 57831399Methyl 4-(3-carboxy-7-cyanoheptyl)benzoate

생성물 1

HCID 57831355Methyl 4-(7-cyano-3-hydroxymethylheptyl)benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

33 ml (33 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 5 g (16.48 mmol) of methyl 4-(3-carboxy-7-cyanoheptyl)benzoate in 62 ml of THF at −15° C., and the solution is stirred at this temperature for 2 hours. Then a further 16 ml (16 mmol) of 1 M borane-THF complex solution are added dropwise at −15° C., and stirring is continued for 45 minutes. The reaction mixture is then warmed to 0° C. and stirred at this temperature for 1 hour. After reaction is complete, 100 ml of saturated bicarbonate solution are added to the reaction mixture, and the solvent is concentrated to dryness. The residue is taken up in ethyl acetate and water, and the aqueous phase is extracted again with ethyl acetate. The combined organic phases are dried over sodium sulfate and again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1→1:3→100% ethyl acetate). 2.4 g (93% purity, 47% of theory) of a colorless solid are obtained.

후처리

  1. additionThen a further 16 ml (16 mmol) of 1 M borane-THF complex solution are added dropwise at −15° C.
  2. stirringstirring
  3. waitis continued for 45 minutes
  4. stirringstirred at this temperature for 1 hour
  5. customAfter reaction
  6. concentrationthe solvent is concentrated to dryness
  7. extractionwater, and the aqueous phase is extracted again with ethyl acetate
  8. dry with materialThe combined organic phases are dried over sodium sulfate
  9. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1→1:3→100% ethyl acetate)
  10. custom2.4 g (93% purity, 47% of theory) of a colorless solid are obtained

출처 및 근거

ORD 기록
ord-c269b15f039044938a6eef81baf1dbf7
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183271B2

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