Water → HCID 131734481, compound

HRID 590520Notes

Reaction equation

HRID 590520 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:13][C:9]2[S:10][CH:11]=[CH:12][C:8]=2[C:7](=[O:14])[CH2:6]1.[CH3:15]I.O>CCCCCC.C1COCC1.[Cl-].[Na+].O>[CH3:15][O:3][CH2:4][C:5]1[CH2:13][C:9]2[S:10][CH:11]=[CH:12][C:8]=2[C:7](=[O:14])[CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 90070459HCID 90070459, compound

Product 1

HCID 131734481HCID 131734481, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.2 g, 5 mmol), was washed with hexane and then suspended in THF (6 mL) under a nitrogen atmosphere at 0° C. 6-(Hydroxymethyl)-6,7-dihydrobenzo[b]thiophen-4(5H)-one (0.745 g, 4.1 mmol) was dissolved in THF (4 mL) and added drop-wise to the sodium hydride suspension. After 10 min methyl iodide (0.71 g, 0.31 mL, 5 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 3 hr. Water and saturated brine solution (2 mL, 1:1) were added and the product was extracted into dichloromethane (×3). The organic layers were combined, dried (MgSO4) and concentrated in vacuo. The crude residue was purified on silica gel using a gradient elution of 0-50% ethyl acetate in iso-hexane to afford the title compound (0.109 g, 34%).

Workup

  1. extractionthe product was extracted into dichloromethane (×3)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified on silica gel using
  5. washa gradient elution of 0-50% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-bf9fbd5e4a134e0ca8938821f8dedc1c
Source dataset
uspto-grants-2016_01
Patent number
US09233982B2

Reaction notes

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