Toluene → 2,2-dimethoxyethyl (S)-6-methoxy-alpha-methyl-2-naphthaleneacetate

HRID 844514ノート

反応式

HRID 844514 の反応式
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][OH:5].CCN(CC)CC.C1(C)C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([C@H:34]([CH3:38])[C:35](Cl)=[O:36])[CH:28]=[CH:27]2>CN(C1C=CN=CC=1)C.O>[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([C@H:34]([CH3:38])[C:35]([O:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])=[O:36])[CH:28]=[CH:27]2

参加物

7

反応物 4

HCID 1140TolueneHCID 8471TriethylamineHCID 5423812,2-DimethoxyethanolHCID 54916922-(6-Methoxynaphthalen-2-yl)propanoyl chloride

生成物 1

HCID 867580112,2-dimethoxyethyl (S)-6-methoxy-alpha-methyl-2-naphthaleneacetate収率 89.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒

実験手順

2,2-Dimethoxyethanol (8.12 g), Et3N (8.99 g), DMAP (80 mg) and toluene (71 mL) are combined and stirred at room temperature. (S)-6-Methoxy-α-methyl-2-naphthaleneacetyl chloride (18.42 g) is added in portions over a period of 8 minutes. The resulting slurry is agitated (35-40° C.) until the reaction is judged to be complete. To the reaction mixture is added water (80 mL) and the phases are separated. The toluene phase is washed with saturated sodium bicarbonate (40 mL) and water (40 mL) and concentrated. Dichloromethane (20 mL) is added and the vacuum evaporation is repeated to produce 21.20 g of 2,2-dimethoxyethyl (S)-6-methoxy-α-methyl-2-naphthaleneacetate.

後処理

  1. stirringThe resulting slurry is agitated (35-40° C.) until the reaction
  2. customthe phases are separated
  3. washThe toluene phase is washed with saturated sodium bicarbonate (40 mL) and water (40 mL)
  4. concentrationconcentrated
  5. additionDichloromethane (20 mL) is added
  6. customthe vacuum evaporation

出典と根拠

ORDレコード
ord-821c55ec22a94befadea3375353b0db2
出典データセット
uspto-grants-2002_04
特許番号
US06380388B1

反応ノート

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