Hydrochloric Acid → HCID 19776906, compound

HRID 1612873Notes

Reaction equation

HRID 1612873 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:11]=3[CH2:10][O:9][C:8](=[O:19])[C:7]=2[C:20]=1[O:21][CH3:22])=[O:2].[C:23]([Mg]Br)(=O)[CH:24]([CH3:26])[CH3:25].Cl>O1CCCC1.C(Cl)Cl>[OH:2][CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:11]=3[CH2:10][O:9][C:8](=[O:19])[C:7]=2[C:20]=1[O:21][CH3:22])[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 19776897HCID 19776897, compoundHCID 178454394HCID 178454394, compound

Product 1

HCID 19776906HCID 19776906, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

660 mg (2.1 mmol) of the compound from Example I in 10 ml of absolute tetrahydrofuran are treated under argon at 0° C. with 1.2 ml (2.3 mmol) of a 2M isobutyryl-magnesium bromide solution in tetrahydrofuran and the mixture is stirred at 25° C. for 1 h. After addition of 2 ml of 1N hydrochloric acid, the mixture is diluted with methylene chloride, washed with water, dried and evaporated. After chromatographic purification on silica gel Si60 (petroleum ether/ethyl acetate 5:1), 121 mg (15% of theory) of the main product are obtained as a colourless solid.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customAfter chromatographic purification on silica gel Si60 (petroleum ether/ethyl acetate 5:1), 121 mg (15% of theory) of the main product
  5. customare obtained as a colourless solid

Sources & evidence

ORD record
ord-e646cf457c1741019162f97ba825375e
Source dataset
uspto-grants-1993_03
Patent number
US05190971

Reaction notes

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