Water → 4-(4-Hydroxybutyl)benzonitrile

HRID 411140ノート

反応式

HRID 411140 の反応式
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)[CH2:2][CH:3]=[CH2:4].O.CC[O:16]CC>C1COCC1.[Cl-].[Na+].O>[OH:16][CH2:4][CH2:3][CH2:2][CH2:1][C:5]1[CH:6]=[CH:7][C:8]([C:9]#[N:10])=[CH:11][CH:12]=1

参加物

6

反応物 3

HCID 962WaterHCID 3283Diethyl EtherHCID 117448814-(3-Butenyl)benzonitrile

生成物 1

HCID 185403804-(4-Hydroxybutyl)benzonitrile

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

4-(3-Butenyl)benzonitrile (from step (i) above, 10.8 g, 69 mmol) was dissolved in dry THF (140 mL) and was cooled to 0° C. BH3—Me2S complex (20 mL, 2 M) was added dropwise over 45 minutes at 0° C. and, after 7 hours, water (70 mL) and NaBO3-4H2O (25 g) were added and the mixture was stirred overnight before dilution with ether (700 mL) and brine (satd., 250 mL). After separation, the aqueous phase was extracted with ether (2×200 mL) and the combined extracts were dried, filtered and evaporated to give crude sub-title compound. Purification by flash chromatography on SiO2 (300 g) with heptane:EtOAc (3:1 to 1:1) gave the sub-title compound (6.99 g).

後処理

  1. additionBH3—Me2S complex (20 mL, 2 M) was added dropwise over 45 minutes at 0° C. and, after 7 hours
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with ether (2×200 mL)
  4. customthe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude sub-title compound
  8. customPurification by flash chromatography on SiO2 (300 g) with heptane:EtOAc (3:1 to 1:1)

出典と根拠

ORDレコード
ord-5630adcc1ed140f6a581e8af3be543cd
出典データセット
uspto-grants-2003_05
特許番号
US06559143B1

反応ノート

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