Ethyl bromoacetate → Ethyl (+/-) 3-(3-methoxyphenyl)indeneacetate

HRID 2299196Notes

Reaction equation

HRID 2299196 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[Li]N([Si](C)(C)C)[Si](C)(C)C.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 156212113-(3-Methoxyphenyl)indeneHCID 178418261HCID 178418261, compound

Product 1

HCID 18340686Ethyl (+/-) 3-(3-methoxyphenyl)indeneacetateYield 19.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold solution of 3-(3-methoxyphenyl)indene (4 g, 18 mmol), prepared by the method of J. Med. Chem. 1981, 24, 998, in THF (15 mL) at 0° C. was added dropwise a solution of LiN(TMS)2 (20 mL, 1M in THF) over 5 min. The resulting solution was added dropwise to a solution of ethyl bromoacetate (3.34 g, 20 mmol) in THF (15 mL) at −78° C. over 30 min. After 2.5 h, the mixture was quenched with saturated ammonium chloride solution and the layers were separated. The organic layer was dried over MgSO4 and concentrated to give the crude product which was purified by column chromatography (SiO2/2-4% EtOAc/hexane) to give title compound (1.1 g): 1H NMR (400 MHz, CDCl3) δ1.30 (t, 3H), 2.50 (m, 1H), 2.85 (m, 1H), 3.85 (s, 3H), 4.0 (m, 1H), 4.20 (q, 2H), 6.6 (s, 1H), 6.9 (m, 1), 7.2 (s, 1H), 7.35 (m, 6H).

Workup

  1. customthe mixture was quenched with saturated ammonium chloride solution
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography (SiO2/2-4% EtOAc/hexane)

Sources & evidence

ORD record
ord-0e0cb656a40f44b0b3218516c3088ed3
Source dataset
uspto-grants-2002_12
Patent number
US06495560B1

Reaction notes

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