Sodium borohydride → (E)-2-(Phenylmethylidene)deca-3,9-diyn-1-ol

HRID 1936913ノート

反応式

HRID 1936913 の反応式
[C:1]1(/[CH:7]=[C:8](\[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])/[CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.[OH-].[Na+]>[C:1]1(/[CH:7]=[C:8](\[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])/[CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 11817217(E)-2-(Phenylmethylidene)deca-3,9-diyn-1-al

生成物 1

HCID 12022749(E)-2-(Phenylmethylidene)deca-3,9-diyn-1-ol収率 91.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of Compound 2 (502 mg, 2.13 mmol) in methanol (20 mL) was added a solution of NaBH4 (80.4 mg, 2.13 mmol) in aqueous NaOH (0.5 N, 5 mL) followed by stirring at room temperature for 30 minutes. The reaction was then quenched with saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (50 mL×2). The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 462.3 mg (91.4 percent) of Compound 3: yellow oil; Rf=0.19 (17 percent EtOAc in hexane); IR (neat) 3400 (br), 3296, 2942, 2862, 2210, 2116, 1072 cm−1; 1H NMR (300 MHz, CDCl3) δ7.84-7.81 (m, 2H), 7.37-7.26 (m, 3H), 6.71 (s, 1H), 4.25 (s, 2H), 2.49 (t, J=6.65 Hz, 2H), 2.24 (td, J=6.78, 2.37 Hz, 2H), 2.17 (br s, 1H), 1.98 (t, J=2.64 Hz, 1H), 1.79-1.60 (m, 4H); 13C NMR (75 MHz, CDCl3) δ136.7, 133.3, 129.1, 128.8, 128.7, 122.5, 98.8, 84.7, 79.3, 69.3, 68.1, 28.2, 28.1, 20.0, 18.6; MS (+CI) m/z (relative intensity) 239 (M+H+, 15), 221 (100); HRMS (+EI) calcd for C17H18O 238.1358 (M+), found 238.1316.

後処理

  1. customThe reaction was then quenched with saturated aqueous NH4Cl (50 mL)
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane)

出典と根拠

ORDレコード
ord-d9d4a7165cfb452ca265d55d215f9f73
出典データセット
uspto-grants-2002_05
特許番号
US06391916B1

反応ノート

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