Triethylsilane → Ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate

HRID 2268443Notes

Reaction equation

HRID 2268443 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:14][C:13]2[C:8](=[C:9]([O:21][CH3:22])[C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[C:12]=2[O:15][CH3:16])[CH:7]1O)=[O:5])[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C:6]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:7][C:8]2[C:13](=[C:12]([O:15][CH3:16])[C:11]([O:17][CH3:18])=[C:10]([O:19][CH3:20])[C:9]=2[O:21][CH3:22])[CH2:14]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 18348646Ethyl 8-(2-ethoxycarbonyl-1-hydroxy-4,5,6,7-tetramethoxyindan-2-yl)octanoate

Product 1

HCID 18348627Ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoateYield 35.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To ethyl 8-(2-ethoxycarbonyl-1-hydroxy-4,5,6,7-tetramethoxyindan-2-yl)octanoate (3.77 g, 7.59 mmols), added was trifluoroacetic acid (40 ml) at room temperature, and then triethylsilane (4.85 ml, 30.4 mmols) was added thereto, and stirred for 15 minutes. The reaction mixture was concentrated in vacuo, a saturated aqueous sodium bicarbonate solution was added thereto, and extracted with ethyl acetate, and the resulting organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 10:1) to obtain the entitled compound (1.31 g) as an oil.

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiona saturated aqueous sodium bicarbonate solution was added
  4. extractionextracted with ethyl acetate
  5. washthe resulting organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and then dried
  7. customThe solvent was evaporated out in vacuo
  8. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-31191b1f24fc4300ba90abf5e6c7a7ea
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…