HCID 2820297, compound → HCID 21184442, compound

HRID 1385283Notes

Reaction equation

HRID 1385283 reaction equation
[C:1]([C:3]1[S:4][C:5](S(C)(=O)=O)=[C:6]2[C:11](=[O:12])[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7]=12)#[N:2].[CH2:19]([Mg]Cl)[CH:20]([CH3:22])[CH3:21]>C1COCC1>[C:1]([C:3]1[S:4][C:5]([CH2:19][CH:20]([CH3:22])[CH3:21])=[C:6]2[C:11](=[O:12])[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7]=12)#[N:2]

Participants

4

Reactant 2

HCID 2820297HCID 2820297, compoundHCID 178418368HCID 178418368, compound

Product 1

HCID 21184442HCID 21184442, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-cyano-6,6-dimethyl-3-methanesulphonyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (1.5 g, 5.3 mmol) in THF (15 mL) at −10° C. was added isobutylmagnesium chloride. After 1 h the cooling bath was removed and the mixture stirred at room temperature for 2 h. After this time the mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol: EtOAc (6:1), to give the title compound (526 mg, 38%) as an orange oil. 1HNMR (360 MHz, CDCl3) δ 0.97 (6H, d, J=6.6 Hz), 1.08 (6H, s), 1.94-2.02 (1H, m), 2,42 (2H, s), 2.85 (2H, s), 3.16 (2H, d, J=7.1 Hz).

Workup

  1. customAfter 1 h the cooling bath was removed
  2. customAfter this time the mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with petrol: EtOAc (6:1)

Sources & evidence

ORD record
ord-b0235d4249394adb8ae1ad9addf5c0b1
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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