Lithium borohydride → HCID 15542191, compound

HRID 1421079Notes

Reaction equation

HRID 1421079 reaction equation
[CH3:1][C:2]1([CH3:25])[O:6][C:5](=[O:7])[C:4]([O:8][CH:9]([CH3:14])[C:10](OC)=[O:11])=[C:3]1[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1.[Li+].[BH4-]>C(Cl)Cl.CCOCC>[OH:11][CH2:10][CH:9]([CH3:14])[O:8][C:4]1[C:5](=[O:7])[O:6][C:2]([CH3:1])([CH3:25])[C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 15542206HCID 15542206, compound

Product 1

HCID 15542191HCID 15542191, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To the ester of Step 1 (1.13 g, 3.07 mmol) in CH2Cl2 (30 mL) and Et2O 50 mL was added at 0∞C. LiBH4 (80 mg, 3.68 mmol). The reaction mixture was stirred at room temperature until completion. The reaction mixture was partitioned between 25% NH4OAc and EtOAc. The organic phase was separated, dried over Na2SO4 and evaporated. The title compound (275 mg) was obtained as a white solid after purification by flash chromatography.

Workup

  1. customThe reaction mixture was partitioned between 25% NH4OAc and EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-8286ac6a13be4b53a5a6f80ccbe314e8
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

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