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

HRID 844514노트

반응식

HRID 844514 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-821c55ec22a94befadea3375353b0db2
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380388B1

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