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

HRID 2268492Notes

Reaction equation

HRID 2268492 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2861c39f953b44c680112f31fae24301
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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