Chloromethyl ethyl ether → HCID 22117148, compound

HRID 1275542Notes

Reaction equation

HRID 1275542 reaction equation
[OH:1][C:2]1[C:3](=[O:26])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(N(C(C)C)CC)(C)C.[CH2:36]([O:38][CH2:39]Cl)[CH3:37]>ClCCl>[CH2:36]([O:38][CH2:39][O:1][C:2]1[C:3](=[O:26])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:37]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 178504197HCID 178504197, compound

Product 1

HCID 22117148HCID 22117148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 2-hydroxy-3-(9-trimethylsilylnonyl)-1,4-naphthoquinone, Example 12, (500 mg, 2.06 mmol) in dry dichloromethane (20 ml) at room temperature was added diisopropylethylamine (1.33 g, 10.3 mmol) and, after 3 minutes, ethoxymethyl chloride (831 mg, 10.3 mmol) in dichloromethane (5 ml). The reaction was stirred for 1 h before diluting with dichloromethane (30 ml), washing with water (2×20 ml), dilute hydrochloric acid (20 ml), saturated sodium chloride solution (20 ml) and drying (MgSO4). Filtration and evaporation of the solvent under reduced pressure and chromatography, eluent hexane/ether, gave 2-ethoxymethoxy-3-(9-trimethylsilylnonyl)-1,4-naphthoquinone (567 mg), nD 1.5182. NMR peaks at: 185.3, 181.6, 155.5, 137.1, 133.8, 133.2, 132.0, 131.4, 126.3, 126.2, 33.6, 30.1, 29.5, 29.4, 29.3, 28.9, 24.1, 23.9, 16.7, -1.6; 96.9, 65.8, 15.0 (O--CH2 --O--CH2CH3).

Workup

  1. washwashing with water (2×20 ml), dilute hydrochloric acid (20 ml), saturated sodium chloride solution (20 ml)
  2. dry with materialdrying (MgSO4)
  3. filtrationFiltration and evaporation of the solvent under reduced pressure and chromatography, eluent hexane/ether

Sources & evidence

ORD record
ord-6f2e1af2879e422e9da733bd8b598703
Source dataset
uspto-grants-2000_12
Patent number
US06162799

Reaction notes

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