Iodoethane → Methyl acetate hexane

HRID 237861

反応式

HRID 237861 の反応式
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]#[C:12][CH2:13][OH:14].I[CH2:16][CH3:17]>CN(C=O)C>[CH3:8][O:3][C:4]([CH3:5])=[O:9].[CH3:4][CH2:5][CH2:6][CH2:7][CH2:16][CH3:17].[CH2:16]([O:14][CH2:13][C:12]#[C:11][CH2:10][O:9][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][O:3]1)[CH3:17]

参加物

6

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 111233154-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

生成物 2

HCID 23449302Methyl acetate hexane収率 1%HCID 685294632-(4-Ethoxy-but-2-ynyloxy)-tetrahydro-pyran

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

An oven dried 500 ml RBF was charged with NaH (60% in mineral oil) (1.41 g, 35.3 mmol) and suspended in DMF (100 mL). The mixture was cooled to 0° C. and 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol (prepared in accordance with the procedures of Tamaru et al., Bull. Chem. Soc. Jpn., 1995, 1689-1705) (6.0 g, 35.3 mmol) was added. The reaction mixture was allowed to reach room temperature and stirred for one hour. To the mixture was added iodoethane (20.8 g, 133 mmol). The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O and extracted with MeOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (1-20% MeOAc/hexane) provided 4.71 g of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran as a clear oil.

後処理

  1. customAn oven dried 500 ml RBF
  2. addition, 1995, 1689-1705) (6.0 g, 35.3 mmol) was added
  3. customto reach room temperature
  4. stirringThe reaction mixture was stirred for 3.5 hours at room temperature
  5. custombefore being quenched with ice/H2O
  6. extractionextracted with MeOAc
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-fd436759d4e74f2f98770a0ccab266a0
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

関連ノート

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