Chloromethyl Methyl Ether → HCID 68649319, compound

HRID 2382525Notes

Reaction equation

HRID 2382525 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]([OH:42])[C@@H:14]1[O:18][C@@H:17]([C@H:19]([OH:41])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C@@H:31]([OH:40])[CH2:32][C:33]2[C:37](=[O:38])[O:36][C@@H:35]([CH3:39])[CH:34]=2)=[O:25])[CH2:16][CH2:15]1.[CH3:43][O:44][CH2:45]Cl>C(N(C(C)C)CC)(C)C>[CH3:43][O:44][CH2:45][O:40][CH:31]([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]([O:41][CH2:35][O:36][CH3:37])[CH:17]1[CH2:16][CH2:15][CH:14]([CH:13]([O:42][CH2:17][O:18][CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:18]1)[CH2:32][C:33]1[C:37](=[O:38])[O:36][CH:35]([CH3:39])[CH:34]=1

Participants

4

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 14456327HCID 14456327, compound

Product 1

HCID 68649319HCID 68649319, compound

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of annonacinone (595 mg, 1.0 mmol) in diisopropylethylamine (7 mL) is stirred at room temperature while chloromethyl methyl ether (360 mg, 4.5 mmol) is added. The mixture is stirred at room temperature for eight hours, concentrated in vacuo, and the residue is partitioned between water (50 mL) and ethyl acetate (50 mL). The aqueous phase is separated and extracted with ethyl acetate (2×50 mL) and the combined organic fractions are washed (1× water), dried (saturated aqueous NaCl, sodium sulfate), filtered, and concentrated. Chromatography (hexane-2:1 hexane:ethyl acetate gradient over silica gel 230-400 mesh) affords 3-{2,13-bis(methoxymethyloxy)-13-[tetrahydro-5-(1-methoxymethyloxytridecyl)furan-2-yl]tridecan-8-on-1-yl}-5-methyl-2-(5H)-furanone.

Workup

  1. additionis added
  2. concentrationconcentrated in vacuo
  3. customthe residue is partitioned between water (50 mL) and ethyl acetate (50 mL)
  4. customThe aqueous phase is separated
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washthe combined organic fractions are washed (1× water)
  7. dry with materialdried (saturated aqueous NaCl, sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8d1d430c200844bfab2ebdc632c93d56
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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