Diisopropylethylamine → HCID 20092833, compound

HRID 274105Notes

Reaction equation

HRID 274105 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[C:14]#[N:15])=[CH:5][CH:4]=1.[O:16]=[C:17]([CH2:24][CH2:25][CH3:26])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(C(C)C)CC)(C)C.[Li+].[Br-]>C1COCC1>[C:14]([C:13]1[CH:12]=[CH:11][S:10][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][CH:18]([C:17](=[O:16])[CH2:24][CH2:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:5]=1)#[N:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 82050Lithium BromideHCID 238498Ethyl 3-oxohexanoateHCID 200928574-(3-Cyano-2-thienyl)benzyl bromide

Product 1

HCID 20092833HCID 20092833, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 50 g of 2-(4-bromomethylphenyl)-3-cyanothiophene, prepared above, 40 g of ethyl 3-oxohexanoate, prepared in Example 1, 300 ml of THF, 62 ml of diisopropylethylamine and 15.6 g of LiBr is refluxed for 15 h. It is concentrated under vacuum, a dilute solution of hydrochloric acid is added and the mixture is extracted with ethyl acetate. The organic phases are combined, washed with water, dried and evaporated to give 62.4 g of ethyl 2-[4-(3-cyano-2-thienyl)benzyl]-3-oxohexanoate in the form of an oil, which is used without further purification.

Workup

  1. temperatureis refluxed for 15 h
  2. concentrationIt is concentrated under vacuum
  3. additiona dilute solution of hydrochloric acid is added
  4. extractionthe mixture is extracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-6eefa74782a0474fae9ec2b2dcb686c2
Source dataset
uspto-grants-1995_02
Patent number
US05387747

Reaction notes

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