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

HRID 1672673ノート

反応式

HRID 1672673 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ddc6fa0f01aa4405b6fa46442f641333
出典データセット
uspto-grants-2011_08
特許番号
US07998988B2

反応ノート

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