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Hydrochloric Acid → 2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethanol

HRID 2268492
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HRID 2268492 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][CH2:12][CH:13]1[CH2:19][CH2:18][C:17]2[C:20]([O:30][CH3:31])=[C:21]([O:28][CH3:29])[C:22]([O:26][CH3:27])=[C:23]([O:24][CH3:25])[C:16]=2[CH2:15][CH2:14]1)(=O)C.Cl>C(OCC)C.O>[CH3:25][O:24][C:23]1[C:16]2[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][OH:10])[CH2:19][CH2:18][C:17]=2[C:20]([O:30][CH3:31])=[C:21]([O:28][CH3:29])[C:22]=1[O:26][CH3:27]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 183485472-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 183486172-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethanol수율 98.4%

시약·촉매·용매 2

HCID 962Water용매
HCID 3283
Diethyl Ether
용매
2회

실험 절차

To a suspension of lithium aluminum hydride (486 mg) in diethyl ether (20 ml) was dropwise added a solution of 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate (3.00 g) in diethyl ether (10 ml) with cooling with ice. After the reaction mixture stirred for 30 min, 10% hydrochloric acid was added to the reaction mixture, which was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:1) to yield the entitled compound (2.60 g) as crystals.

후처리

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-2861c39f953b44c680112f31fae24301
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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