Acetic Acid → Ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propanoate

HRID 34470

반응식

HRID 34470 반응식
[C:1]([C:3](=[CH:9][C:10]1[C:15]2[CH:16]=[CH:17][CH2:18][O:19][C:14]=2[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C(O)(=O)C.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C([BH3-])#N.[Na+]>C(O)C>[C:1]([CH:3]([CH2:9][C:10]1[C:15]2[CH:16]=[CH:17][CH2:18][O:19][C:14]=2[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

참가 물질

6

반응물 4

HCID 176Acetic Acid3회HCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 54507081Ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propenoate

생성물 1

HCID 20129780Ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propanoate

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A mixture of ethyl 2-cyano-3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)propenoate (19.8 g, 0.63 mole) in ethanol (500 mL) under nitrogen was treated with acetic acid (4 mL) and a trace of bromocresol green and heated to reflux. Heating was discontinued and sodium cyanoborohydride (4.4 g, 0.07 mole) in ethanol (100 mL) was co-added with additional acetic acid (11 mL). The mixture was stirred under nitrogen for 2 hr, acetic acid (10 mL) added and the ethanol removed under reduced pressure. The resultant yellow solid was taken up in ethyl acetate (250 mL) and successively extracted with water (125 mL), saturated sodium bicarbonate (3×100 mL) and water (100 mL), then dried over magnesium sulfate. The volatiles were removed under reduced pressure to leave an amber oil, 18.22 g (91.4%) which was used without further purification.

후처리

  1. temperatureHeating
  2. customthe ethanol removed under reduced pressure
  3. extractionsuccessively extracted with water (125 mL), saturated sodium bicarbonate (3×100 mL) and water (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe volatiles were removed under reduced pressure
  6. customto leave an amber oil, 18.22 g (91.4%) which
  7. customwas used without further purification

출처 및 근거

ORD 기록
ord-62b182c93158406b8248468834a06f6a
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761475

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