HCID 15056951, compound → HCID 15056952, compound

HRID 2165134Notes

Reaction equation

HRID 2165134 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]([C:19](OC)=[O:20])[C:17]([CH3:24])([CH3:23])[CH2:16][C:10]3([S:15][CH2:14][CH2:13][CH2:12][S:11]3)[CH:9]=2)=[CH:4][C:3]=1[CH3:25].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]([CH2:19][OH:20])[C:17]([CH3:23])([CH3:24])[CH2:16][C:10]3([S:11][CH2:12][CH2:13][CH2:14][S:15]3)[CH:9]=2)=[CH:4][C:3]=1[CH3:25]

Participants

4

Reactant 2

HCID 15056951HCID 15056951, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15056952HCID 15056952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5 (7.77 g, 20.4 mmol) in 80 mL of anhydrous THF at 0°-5° C. was added portionwise LAH (0.97 g, 25.6 mmol). The mixture was stirred for 1.5 h, quenched with 1 mL of H2O, 1 mL of 15% NaOH and 3 mL of H2O and filtered. The volatiles were removed in vacuo and the residue recrystallized with hexanes:EtOAc. Wt. 5.55 g. mp 128°-129° C. Anal. C19H25FOS2 ; Theory C: 64.74; H: 7.15; S:18.19. Found C:. 64.57; H: 7.03; S: 17.71.

Workup

  1. customquenched with 1 mL of H2O, 1 mL of 15% NaOH and 3 mL of H2O
  2. filtrationfiltered
  3. customThe volatiles were removed in vacuo
  4. customthe residue recrystallized with hexanes

Sources & evidence

ORD record
ord-c21243b079d64fee8c4cedb5dff80caa
Source dataset
uspto-grants-1990_07
Patent number
US04939143

Reaction notes

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