Lithium borohydride → HCID 20636304, compound

HRID 49357Notes

Reaction equation

HRID 49357 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:19](OC)=[O:20])[C:12](=[CH:17][CH:18]=2)[C:13](OC)=[O:14])[S:4][CH:3]=1.[BH4-].[Li+]>C1COCC1>[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][C:12]([CH2:13][OH:14])=[C:11]([CH2:19][OH:20])[CH:10]=2)[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 20636315HCID 20636315, compound

Product 1

HCID 20636304HCID 20636304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

27 g (76 mmol) of dimethyl 4-(3-bromo-5-thienylmethoxy)phthalate are dissolved in 200 mL of anhydrous THF. This solution is added dropwise to a suspension of 4 g (183 mmol) of lithium borohydride in 50 mL of THF. The reaction medium is refluxed for 24 h and then cooled and poured onto 200 g of ice. After extraction with ether and then chromatography on a column of silica (eluent: 5 heptane/5 ethyl acetate), the desired product is obtained in the form of a yellow oil (m=22.1 g; Y=88%).

Workup

  1. temperatureThe reaction medium is refluxed for 24 h
  2. temperaturecooled
  3. extractionAfter extraction with ether

Sources & evidence

ORD record
ord-bf5fb956ca4940e0b7310b4fc4c65eda
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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