1-(Chloromethoxy)-2-methoxyethane → HCID 20194721, compound

HRID 653442Notes

Reaction equation

HRID 653442 reaction equation
[OH:1][CH:2]1[CH2:8][CH2:7][CH2:6][S:5][C:4]2[CH:9]=[CH:10][S:11][C:3]1=2.C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26]Cl>C(Cl)Cl>[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][O:1][CH:2]1[CH2:8][CH2:7][CH2:6][S:5][C:4]2[CH:9]=[CH:10][S:11][C:3]1=2

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 13911644HCID 13911644, compound

Product 1

HCID 20194721HCID 20194721, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-hydroxy-5,6,7,8-tetrahydrothieno[3,2-b]thiepin (16.6 g, 0.089 mole) and diisopropylethylamine (18.1 g, 0.14 mole) in methylene chloride (185 ml) was added β-methoxyethoxymethyl chloride (17.5 g, 0.14 mole) over 10 minutes under nitrogen at ambient temperature. The solution was stirred for 117 hours and then washed with cold 0.5N HCl (2×100 ml), saturated sodium bicarbonate solution, twice with water and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel (2.5 kg), eluting with 20% ethyl acetate-hexane (v/v), to yield 19.97 g (82%) of oily product.

Workup

  1. washwashed with cold 0.5N HCl (2×100 ml), saturated sodium bicarbonate solution, twice with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was chromatographed on silica gel (2.5 kg)
  5. washeluting with 20% ethyl acetate-hexane (v/v)

Sources & evidence

ORD record
ord-e6db5e2426b246d9af622f6eaf08a026
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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