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

HRID 377763Notes

Reaction equation

HRID 377763 reaction equation
[BH4-].[Li+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)/[C:10](=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1)/[C:9]([CH3:25])=[C:8]2[CH2:26][C:27](Cl)=[O:28]>C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)/[C:10](=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][CH:16]=1)/[C:9]([CH3:25])=[C:8]2[CH2:26][CH2:27][OH:28]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86755164(Z)-5-Methoxy-2-methyl-1-(4-methylsulfonylbenzylidene)-3-indenylacetyl chloride

Product 1

HCID 70289997(Z)-5-Methoxy-2-methyl-1-(4-methylsulfonylbenzylidene)-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 a solution of (Z)-5-methoxy-2-methyl-1-(4-methylsulfonylbenzylidene)-3-indenylacetyl chloride (2.78 mmol) in THF (20 ml) at 0° C. The reaction is quenched with HCl (10%, aqueous, 30 ml) after 5 minutes. Ethyl acetate (50 ml) is added to extract the product.

Workup

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

Sources & evidence

ORD record
ord-adac3721e4f5423a8e21e4294a7fd1fd
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Reaction notes

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