2-Chloroethanol → HCID 86753801, compound

HRID 1417607Notes

Reaction equation

HRID 1417607 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:8][CH2:9][OH:10].[CH2:11]([O:18][C:19]1[C:20]2[CH2:31][C@:30]3([CH3:44])[C@@H:32]([CH3:43])[CH2:33][CH2:34][C@H:35]4[C:36]([CH3:42])([CH3:41])[C@@H:37]([OH:40])[CH2:38][CH2:39][C@@:29]34[O:28][C:21]=2[C:22]2[CH2:23][NH:24][CH2:25][C:26]=2[CH:27]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C=O)C>[CH2:11]([O:18][C:19]1[C:20]2[CH2:31][C@:30]3([CH3:44])[C@@H:32]([CH3:43])[CH2:33][CH2:34][C@H:35]4[C:36]([CH3:42])([CH3:41])[C@@H:37]([OH:40])[CH2:38][CH2:39][C@@:29]34[O:28][C:21]=2[C:22]2[CH2:23][N:24]([CH2:8][CH2:9][OH:10])[CH2:25][C:26]=2[CH:27]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 10340Sodium CarbonateHCID 86753797HCID 86753797, compound

Product 1

HCID 86753801HCID 86753801, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Under nitrogen, 35 mg (0.25 mmol) of sodium carbonate and 23 μl (0.33 mmol) of 2-chloroethanol were added to a solution of Compound (33a) (40 mg, 0.087 mmol) in dry DMF (0.5 ml). The mixture was stirred for 3 hours at 50° C. and then for 18 hours at 65° C. After cooling, water was added to the reaction, and extracted with ethyl acetate. The extract was washed with water, saturated brine, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the resulting residue was purified by a silica gel column chromatography (silica gel 1.5 g; chloroform:methanol=19: 1) to give 25 mg (57%) of Compound (33f).

Workup

  1. waitfor 18 hours at 65° C
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water, saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (silica gel 1.5 g; chloroform:methanol=19: 1)

Sources & evidence

ORD record
ord-5c6e2a82a6e84d1292ccfc49d8e65e04
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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