Lithium borohydride → (Z)-1-(4-methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-1H-3-indenyl-(2-hydroxy)ethane

HRID 377760Notes

Reaction equation

HRID 377760 reaction equation
[BH4-].[Li+].[CH3:3][S:4]([C:7]1[CH:30]=[CH:29][C:10](/[CH:11]=[C:12]2/[C:13]([CH3:28])=[C:14]([CH2:24][C:25](Cl)=[O:26])[C:15]3[C:20]/2=[CH:19][CH:18]=[C:17]([N:21]([CH3:23])[CH3:22])[CH:16]=3)=[CH:9][CH:8]=1)(=[O:6])=[O:5]>C1COCC1>[CH3:3][S:4]([C:7]1[CH:8]=[CH:9][C:10](/[CH:11]=[C:12]2/[C:13]([CH3:28])=[C:14]([CH2:24][CH2:25][OH:26])[C:15]3[C:20]/2=[CH:19][CH:18]=[C:17]([N:21]([CH3:22])[CH3:23])[CH:16]=3)=[CH:29][CH:30]=1)(=[O:5])=[O:6]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86755163(Z)-1-(4-Methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-3-indenylacetyl chloride

Product 1

HCID 70289986(Z)-1-(4-methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-1H-3-indenyl-(2-hydroxy)ethane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium borohydride (1.38 mmol) in THF (2 ml) is added to the solution of (Z)-1-(4-methylsulfonylbenzylidene)-5-dimethylamino-2-methyl-3-indenylacetyl chloride (2.78 mmol) in THF (20 ml) at 0° C. The reaction is quenched with HCl after 5 minutes (10%, aqueous, 30 ml). Ethyl acetate (50 ml) is added to extract the product.

Workup

  1. customThe reaction is quenched with HCl after 5 minutes (10%, aqueous, 30 ml)
  2. additionEthyl acetate (50 ml) is added
  3. extractionto extract the product

Sources & evidence

ORD record
ord-a302ced4f05b4b38a1ad13d65ef75c7d
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Reaction notes

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