Hexane → HCID 69074334, compound

HRID 389009Notes

Reaction equation

HRID 389009 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:10]=[CH:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:7]=1.[Li+].[BH4-].CCCCCC.C(OCC)(=O)C>C1COCC1>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([S:11]([N:8]2[CH:9]=[CH:10][C:6]([CH:5]=[CH:4][CH2:3][OH:2])=[CH:7]2)(=[O:13])=[O:12])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 69071973HCID 69071973, compound

Product 1

HCID 69074334HCID 69074334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 13 (3 g, 10 mmol) in 150 mL anhydrous THF was added LiBH4 (0.27 g, 12 mmol) under nitrogen and the mixture was stirred at room temperature for 24 h. The reaction was quenched by the addition of 1 M H2SO4 solution. The resulting solution was extracted with dichloromethane. The extracts were washed with saturated aqueous sodium bicarbonate, water and brine, dried over sodium sulphate, filtered and evaporated under vacuum to give light yellow solid which subjected to flash chromatography (silica gel, hexane:ethyl acetate=2:1) to afford 14.

Workup

  1. customThe reaction was quenched by the addition of 1 M H2SO4 solution
  2. extractionThe resulting solution was extracted with dichloromethane
  3. washThe extracts were washed with saturated aqueous sodium bicarbonate, water and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto give light yellow solid which

Sources & evidence

ORD record
ord-40087cb42e324a1aac55033ccd93fec1
Source dataset
uspto-grants-2013_02
Patent number
US08378058B2

Reaction notes

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