Dimethyl Sulfoxide → 3-(3-Chloro-benzo[b]thiophen-2-yl)-propionaldehyde

HRID 406799Notes

Reaction equation

HRID 406799 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[C:13]2[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=2[S:15][C:16]=1[CH2:17][CH2:18][CH2:19][OH:20].C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[C:13]2[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=2[S:15][C:16]=1[CH2:17][CH2:18][CH:19]=[O:20]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 219644313-(3-Chloro-benzo[b]thiophen-2-yl)-propan-1-ol

Product 1

HCID 219644333-(3-Chloro-benzo[b]thiophen-2-yl)-propionaldehydeYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A −78° C. solution of oxalyl chloride (1.73 g, 13.6 mmol) in dichloromethane (20 mL) was treated with DMSO (20 mL). After 5 min., a solution of alcohol 16 (2.57 g, 11.3 mmol) in dichloromethane (20 mL) was added. After another 15 min., triethylamine (7.1 mL, 50.6 mmol) was added. The reaction was stirred at −78° C. for 5 min., and then allowed to warm to room temperature. After 30 min., 100 mL water was added and the mixture extracted with dichloromethane (3×60 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (10% ethyl acetate/hexane) gave 2.11 g (9.4 mmol, 83%) of the aldehyde (17).

Workup

  1. waitAfter another 15 min.
  2. temperatureto warm to room temperature
  3. waitAfter 30 min.
  4. extractionthe mixture extracted with dichloromethane (3×60 mL)
  5. dry with materialThe combined dichloromethane solution was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography on silica gel (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-957d2e30a0d341479f9f10bd51a6ce5e
Source dataset
uspto-grants-2014_06
Patent number
US08754122B2

Reaction notes

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