Chloromethyl Methyl Ether → HCID 18630303, compound

HRID 376637Notes

Reaction equation

HRID 376637 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Si:21]([CH3:24])([CH3:23])[CH3:22])[CH3:12].[CH3:26][O:27][CH2:28]Cl>C1COCC1>[CH2:11]([N:13]([CH2:26][O:27][CH3:28])[C:14](=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Si:21]([CH3:24])([CH3:23])[CH3:22])[CH3:12]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18630201HCID 18630201, compound

Product 1

HCID 18630303HCID 18630303, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M THF solution of sodium bis(trimethylsilyl)amide (52.5 mL, 52.5 mmol) was added dropwise over 5 min to a solution of the compound of Example 49 (11.07 g, 50 mmol) in THF (100 mL). The resulting mixture was cooled with a dry ice/acetone bath while neat chloromethyl methyl ether (4.83 g, 60 mmol) was added, maintaining the internal reaction temperature <-70° C. The cold bath was removed and the resulting reaction mixture was allowed to warm for 1 h, then was partitioned between sat aq NaHCO3 and ether. The ether phase was dried (MgSO4), concentrated, and purified by HPLC with 3:17 ethyl acetate/hexanes to afford 6.55 g of the title compound as a colorless oil, a 49% yield.

Workup

  1. additionwas added
  2. temperaturemaintaining the internal reaction temperature <-70° C
  3. customThe cold bath was removed
  4. customthe resulting reaction mixture
  5. temperatureto warm for 1 h
  6. customwas partitioned
  7. dry with materialThe ether phase was dried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by HPLC with 3:17 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-22fcf9311c3945d18918d1ffa8c19861
Source dataset
uspto-grants-2000_02
Patent number
USRE036562

Reaction notes

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