Water → 4-(4-Hydroxybutyl)benzonitrile

HRID 500472ノート

反応式

HRID 500472 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-MeS 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-MeS 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-3cca8789cea24fc6b4ed91856072d820
出典データセット
uspto-grants-2010_08
特許番号
US07772229B2

反応ノート

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