Water → ethyl-5-(2-Methyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoate

HRID 1860539Notes

Reaction equation

HRID 1860539 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14].[CH2:15]([O:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22]Br)[CH3:16].O>C1COCC1>[CH2:15]([O:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][C:4]1([CH3:3])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 1026502-Methyl-1-tetralone

Product 1

HCID 18623285ethyl-5-(2-Methyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 0.86 g NaH in 40 mL of dry THF are added 5.0 g 2-methyl-1-tetralon in 20 mL of THF. After stirring for 30 min, 7.5 g ethyl-5-bromo-pentanoate in 20 mL of THF are added and the mixture is refluxed for 6 h. The cooled mixture is poured into water and extracted with ethylacetate. The extract is evaporated yielding crude ethyl-5-(2-Methyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoate (6a) which is purified by column chromatography, yielding 3.6 g of pure 6a. 6a is converted to 6b in an analogous manner to that described for the conversion of 1c to 1d in example 1. 6b was obtained as an oil, MS (APCI): 274.1 (M−1).

Workup

  1. temperaturethe mixture is refluxed for 6 h
  2. extractionextracted with ethylacetate
  3. customThe extract is evaporated

Sources & evidence

ORD record
ord-30bf41e774ed46b18230e86df1ef9dda
Source dataset
uspto-grants-2003_03
Patent number
US06531472B2

Reaction notes

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