Dimethylformamide → HCID 68180680, compound

HRID 2276912Notes

Reaction equation

HRID 2276912 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:15]=[CH:14][C:10]2[CH:11]=[CH:12][S:13][C:9]=2[CH:8]=1.CS(O[CH2:21][CH:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O>[CH3:27][C:24]1([CH3:28])[O:23][CH:22]([CH2:21][O:6][C:7]2[CH:15]=[CH:14][C:10]3[CH:11]=[CH:12][S:13][C:9]=3[CH:8]=2)[CH2:26][O:25]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 88004Benzo(b)thiophene-6-olHCID 15570840(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate

Product 1

HCID 68180680HCID 68180680, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Dimethylformamide (10 mL) was added to a reactor containing 6-hydroxybenzothiophene (22, 619 mg, 4.12 mmol), (R/S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate ((R/S)-18a, 1.04 g, 4.95 mmol) and Cs2CO3(1.61 g, 4.95 mmol). The reaction mixture was agitated at 100° C. for 6 hours and then cooled to room temperature. After adding water, extracting with ethyl acetate, washing with saturated ammonium chloride aqueous solution, and removing water using sodium sulfate, column chromatography yielded 6-[(R/S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyloxy]benzothiophene ((R/S)-25, 1.08 g, 99%) as a liquid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracting with ethyl acetate
  3. washwashing with saturated ammonium chloride aqueous solution
  4. customremoving water

Sources & evidence

ORD record
ord-3545713035d342cfb0a0392adb3e0737
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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