Ammonium Chloride → 3-Ethynylbenzenemethanol

HRID 720117ノート

反応式

HRID 720117 の反応式
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])(C)C.[F-].[K+].[BH4-].[Na+].[NH4+].[Cl-]>CO>[C:6]([C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=1)#[CH:5]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 522689Potassium FluorideHCID 27716423-(Trimethylsilyl)ethynylbenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 154687703-Ethynylbenzenemethanol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
22 °C

実験手順

To 3-trimethylsilanylethynyl-benzaldehyde 73(a1) from step 1a in methanol (540 mL, 0.3 M) was added KF (18.8 g, 324 mmol), and the resulting mixture stirred at 22° C. for 6 hours. After cooling to 0° C., NaBH4 (6.13 g, 162 mmol) was carefully added over 0.5 hours. Aqueous saturated NH4Cl was carefully added and the volatiles were removed in vacuo. Ethyl acetate (200 mL) was added, and the organic phase was washed with water and a saturated aqueous NaCl solution, dried over MgSO4 and filtered. The volatiles were removed in vacuo to afford crude (3-ethynyl-phenyl)-methanol 73(a2).

後処理

  1. temperatureAfter cooling to 0° C.
  2. customthe volatiles were removed in vacuo
  3. additionEthyl acetate (200 mL) was added
  4. washthe organic phase was washed with water
  5. dry with materiala saturated aqueous NaCl solution, dried over MgSO4
  6. filtrationfiltered
  7. customThe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-e870517df16449a9a7a25d74ab0bece6
出典データセット
uspto-grants-2006_11
特許番号
US07132533B2

反応ノート

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