Hydrochloric Acid → HCID 15860332, compound

HRID 377361

Reaction equation

HRID 377361 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH3:11])=[C:5]2[CH2:12][CH2:13][OH:14].[CH3:15][S:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)(=[O:18])=[O:17].C[O-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:23]\[C:22]1[CH:21]=[CH:20][C:19]([S:16]([CH3:15])(=[O:18])=[O:17])=[CH:26][CH:25]=1)/[C:6]([CH3:11])=[C:5]2[CH2:12][CH2:13][OH:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2203764-(Methylsulfonyl)benzaldehydeHCID 10942334Sodium MethoxideHCID 139332935-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy) ethane

Product 1

HCID 15860332HCID 15860332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Fluoro-2-methyl-1H-3-indenyl-(2-hydroxy) ethane (15 g, 0.072 mol), p-methylsulfonylbenzaldehyde (14.0 g, 0.091 mol) and sodium methoxide (13.0 g, 0.24 mol) are heated in methanol (200 ml) at 60° C. under nitrogen with stirring for 6 hours. The reaction mixture is poured onto ice-water (750 g), and is acidified with 2.5N hydrochloric acid. The collected solid is triturated with a little ether to produce (Z)-5-fluoro-2-methyl-1-(p-methylsulfonylbenzylidene)-1H-3-indenyl-(2-hydroxy) ethane. Recrystallization of the crude reaction product results in the separation of the mixture of geometrical isomers (Z/E) and gives the title compound (R1 =5-fluror, R2 =CH3, R3 =H, R4 =CH2OH, n=1, R5 =CH3SO2).

Workup

  1. additionThe reaction mixture is poured onto ice-water (750 g)
  2. customThe collected solid is triturated with a little ether

Sources & evidence

ORD record
ord-0c443b68506842a49d541f85a1283d38
Source dataset
uspto-grants-2000_02
Patent number
US06025394

Linked notes

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