Triethylsilane → Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate

HRID 2268458Notes

Reaction equation

HRID 2268458 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:23][C:22]3[C:17](=[C:18]([O:30][CH3:31])[C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[C:21]=3[O:24][CH3:25])[CH:16]2O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:16][C:17]3[C:22](=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[C:19]([O:28][CH3:29])[C:18]=3[O:30][CH3:31])[CH2:23]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 18348579Ethyl 2-(4-benzyloxyphenyl)-1-hydroxy-4,5,6,7-tetramethoxy-2-indancarboxylate

Product 1

HCID 18348586Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylateYield 59.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (30 ml) was added to ethyl 2-(4-benzyloxyphenyl)-1-hydroxy-4,5,6,7-tetramethoxy-2-indancarboxylate (3.02 g, 5.94 mmols) with cooling with ice, and then triethylsilane (3.80 ml, 23.8 mmols) was added thereto at room temperature. The reaction mixture was stirred for 30 minutes, and then concentrated in vacuo. The residue was diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 8:1) to obtain the entitled compound (1.73 g) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. customat room temperature
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washthe organic layer was washed with a saturated aqueous sodium bicarbonate solution, water
  6. dry with materiala saturated aqueous sodium chloride solution, and then dried
  7. customThe solvent was evaporated out
  8. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 8:1)

Sources & evidence

ORD record
ord-dfc2ac2c78254bbe82a32e9fbe3709a4
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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