Lithium borohydride → (Z)-5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-1H-3-indenyl-(2-hydroxy)ethane

HRID 377755Notes

Reaction equation

HRID 377755 reaction equation
[BH4-].[Li+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)/[C:9](=[CH:13]\[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)/[C:8]([CH3:26])=[C:7]2[CH2:27][C:28](Cl)=[O:29]>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)/[C:9](=[CH:13]\[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)/[C:8]([CH3:26])=[C:7]2[CH2:27][CH2:28][OH:29]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86755162(Z)-5-Fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetyl chloride

Product 1

HCID 70289024(Z)-5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-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 suspension of (Z)-5-Fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetyl chloride (2.78 mmol) in THF (20 ml) at 0° C. The reaction is quenched after 5 minutes with HCl (10%, aqueous, 30 ml). Ethyl acetate (50 ml) is added in order to extract the product. The organic layer is washed with water (2×50 ml), is dried over Na2SO4 and is evaporated to give the title compound, which is purified with flash chromatography (ethylacetate:hexane 8:2). (R1 =F, R2 =CH3, R3 =H, R4 =H, Y=3,4,5-trimethoxyphenyl, n=1, R5 and R6 form a double bond, R7 =H, m=1, p=1).

Workup

  1. customThe reaction is quenched after 5 minutes with HCl (10%, aqueous, 30 ml)
  2. additionEthyl acetate (50 ml) is added in order
  3. extractionto extract the product
  4. washThe organic layer is washed with water (2×50 ml)
  5. dry with materialis dried over Na2SO4
  6. customis evaporated

Sources & evidence

ORD record
ord-72ef397c716046c589fa961c1b3afee5
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Reaction notes

Loading…