Sodium Bicarbonate → Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate

HRID 1672673노트

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HRID 1672673 반응식
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[C:10](O)=[O:11])[CH3:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH:9]([CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:23])=[CH:20][CH:19]=1)#[N:22]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 578313802-[2-(4-Cyanophenyl)ethyl]heptanedioic acid 7-ethyl ester

생성물 1

HCID 57831363Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

54.19 ml of a 1 M borane-THF complex solution (54.19 mmol) are added dropwise to a solution of 8.6 g (27.1 mmol) of 2-[2-(4-cyanophenyl)ethyl]heptanedioic acid 7-ethyl ester from Example 84A in 200 ml of THF at −10° C. After warming to 0° C., the mixture is stirred at this temperature for 2 hours. After reaction is complete, saturated sodium bicarbonate solution is added to the reaction mixture, and the solvent is concentrated to dryness. The residue is taken up in dichloromethane, dried over sodium sulfate and again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10→1:4). 5.1 g (97% purity, 60% yield) of a colorless solid are obtained.

후처리

  1. customAfter reaction
  2. concentrationthe solvent is concentrated to dryness
  3. dry with materialdried over sodium sulfate
  4. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10→1:4)
  5. custom5.1 g (97% purity, 60% yield) of a colorless solid are obtained

출처 및 근거

ORD 기록
ord-ddc6fa0f01aa4405b6fa46442f641333
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998988B2

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