Tetrahydrofuran → Ethyl 10-(6-bromo-2,3,4,5-tetramethoxyphenyl)-9,9-diethoxycarbonyldecanoate

HRID 2268441Notes

Reaction equation

HRID 2268441 reaction equation
C1COCC1.[CH2:6]([O:8][C:9]([CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[CH3:7].[H-].[Na+].[Br:31][C:32]1[C:37]([CH2:38]Br)=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47]>[Cl-].[NH4+]>[Br:31][C:32]1[C:37]([CH2:38][C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 183486201-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzeneHCID 18348648Ethyl 2,9-diethoxycarbonylnonanoate

Product 1

HCID 18348563Ethyl 10-(6-bromo-2,3,4,5-tetramethoxyphenyl)-9,9-diethoxycarbonyldecanoateYield 65.6%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

A THF (10 ml) solution of ethyl 2,9-diethoxycarbonylnonanoate (8.86 g, 26.8 mmols) was dropwise added to a THF (90 ml) suspension of sodium hydride (60% oily, 1.29 g, 32.2 mmols) at room temperature. The reaction mixture was stirred for 2 hours, and then a THF (10 ml) solution of 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (10.9 g, 29.5 mmols) was dropwise added at room temperature, and stirring was continued for additional 2 hours. The reaction mixture was diluted with a saturated aqueous ammonium chloride solution and then concentrated in vacuo. The residue was extracted with ethyl acetate, and the resulting organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The crude product thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1) to obtain the entitled compound (10.9 g) as an oil.

Workup

  1. stirringstirring
  2. waitwas continued for additional 2 hours
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe resulting organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated in vacuo
  8. customThe crude product thus obtained
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1)

Sources & evidence

ORD record
ord-c4c97b25ee6b480188671156d1539fe8
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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