Dichloromethane → HCID 83885318, compound

HRID 1053794Notes

Reaction equation

HRID 1053794 reaction equation
[CH3:1][C:2]([O:4]I1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[S:23]1[CH:27]=[CH:26][C:25]2[CH:28]=[CH:29][C:30](CCO)=[CH:31][C:24]1=2.C([O-])(O)=O.[Na+].C(Cl)[Cl:41]>>[Cl:41][C:26]1[C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[S:23][C:27]=1[CH2:1][CH:2]=[O:4]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 22666345HCID 22666345, compound

Product 1

HCID 83885318HCID 83885318, compound

Procedure

Dess-Martin period inane (1.570 g, 3.70 mmol) was added to an ice-cold solution of 2-(benzo[b]thiophen-6-yl)ethanol (649 mg, 3.05 mmol) in CH2Cl2 (8 mL). The reaction was allowed to warm to room temperature and after 2 h, was poured into a mixture of 50 mL saturated NaHCO3/50 mL 5% NaHSO3 solution. The resulting mixture was stirred for 30 minutes and then was extracted with CH2Cl2 (3×40 mL). The combined organic solution was dried (Na2SO4), filtered and evaporated to give the title compound which was used directly in the next step.

Workup

  1. extractionwas extracted with CH2Cl2 (3×40 mL)
  2. dry with materialThe combined organic solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-974d3063d1a943d28ff599f8ef8ef745
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

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