2-Chloroethanol → 2-Chloroethyl monomethoxytrityl ether

HRID 1709740Notes

Reaction equation

HRID 1709740 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].[CH3:5][O:6][C:7]1[CH:26]=[CH:25][CH:24]=[CH:23][C:8]=1[C:9](Cl)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>N1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:26]=[CH:25][CH:24]=[CH:23][C:8]=1[C:9]([O:4][CH2:3][CH2:2][Cl:1])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 962WaterHCID 14429619Methoxytrityl chloride

Product 1

HCID 230366832-Chloroethyl monomethoxytrityl etherYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chloroethanol (4.02 ml, 60 mmol) and monomethoxytrityl chloride (9.2643 g, 30 mmol) were stirred in pyridine (150 ml) at room temperature for 3 hours. Cold water (15 ml) was added to the reaction solution and the mixture was stirred for 30 minutes, and the reaction mixture was extracted with chloroform (500 ml) and washed with water (200 ml ×3 times). The organic layer was dried with anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate was distilled under a reduced pressure. n-Hexane (100 ml) was added to the residue to effect crystallization, and thus 9.6307 g (yield=91%) of 2-chloroethyl monomethoxytrityl ether <1> was obtained.

Workup

  1. extractionthe reaction mixture was extracted with chloroform (500 ml)
  2. washwashed with water (200 ml ×3 times)
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customThe magnesium sulfate was removed by filtration
  5. distillationthe filtrate was distilled under a reduced pressure
  6. additionn-Hexane (100 ml) was added to the residue
  7. customcrystallization

Sources & evidence

ORD record
ord-7cf7b2c7bd0c4c1db6f62d8d860b3297
Source dataset
uspto-grants-1990_08
Patent number
US04950745

Reaction notes

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