Acetic Anhydride → HCID 11725738, compound

HRID 1376193Notes

Reaction equation

HRID 1376193 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:19]=[O:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([Mg]Cl)=[CH2:22].[C:25](OC(=O)C)(=[O:27])[CH3:26]>O1CCCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:19]([O:20][C:25](=[O:27])[CH3:26])[CH:21]=[CH2:22])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 27762231-(Phenylsulfonyl)-1H-indole-2-carbaldehydeHCID 178461836HCID 178461836, compound

Product 1

HCID 11725738HCID 11725738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2.9 g (10 mmol) of 1-benzenesulfonyl-1H-indole-2-carbaldehyde (synthesized analogous to M. G. Saulnier, G. W. Gordon, J.Org.Chem.; 47; 5; 1982, 757–761) in 10 ml of tetrahydrofuran was added 6.5 ml of vinylmagnesium chloride 1.7 M solution in THF at −20° C. within 1 h. The temperature increased to 0° C. within 30 min and kept at this temperature for 20 min. To the suspension 1.3 ml acetic anhydride (14 mmol was added at 0° C. within 15 min. The cooling bath was removed and after stirring for 1 h at 20° C. 10 ml water was added at 10–15° C. The mixture was stirred for an additional 1 h at 20° C. The phases were separated, and the aqueous phase was extracted with 20 ml of ethyl acetate. The combined organic phases were washed with 20 ml of brine, dried on sodium sulfate and rotary evaporated (35° C., 12 mbar). The crude material was purified by liquid chromatography (eluent isohexane/ethyl acetate 9:1).

Workup

  1. customThe cooling bath was removed
  2. addition10 ml water was added at 10–15° C
  3. stirringThe mixture was stirred for an additional 1 h at 20° C
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with 20 ml of ethyl acetate
  6. washThe combined organic phases were washed with 20 ml of brine
  7. customdried on sodium sulfate
  8. customrotary evaporated (35° C., 12 mbar)
  9. customThe crude material was purified by liquid chromatography (eluent isohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-0b0fdbb3f5a1423598063a937ff741c4
Source dataset
uspto-grants-2007_01
Patent number
US07169935B2

Reaction notes

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