Chloromethyl Methyl Ether → HCID 66663661, compound

HRID 2190204Notes

Reaction equation

HRID 2190204 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([C@@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl[CH2:33][O:34][CH3:35]>C1COCC1>[CH2:11]([C@@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:31])[C@H:25]([CH2:33][O:34][CH3:35])[CH2:26][CH2:27][CH2:28][CH2:29][Br:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 59557990HCID 59557990, compound2×

Product 1

HCID 66663661HCID 66663661, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a round-bottom flask containing THF (80 ml) cooled to −78° C. and purged with a continuous stream of N2 gas was added KHMDS (1 M in THF, 22.6 ml, 4 eq.). In a separate flask purged with a continuous stream of N2 gas was added (R)-4-benzyl-3-(6-bromohexanoyl)oxazolidin-2-one (2.00 g, 1 eq.) dissolved in THF (10 ml) and cooled to −78° C. The solution containing (R)-4-benzyl-3-(6-bromohexanoyl)oxazolidin-2-one was transferred to the KHMDS solution, and chloro(methoxy)methane (7.2 g, 15.8 eq.) was added dropwise. The reaction mixture was allowed to stir for an additional 2 h, quenched with saturated aqueous NH4Cl and concentrated. Water was added. The mixture was extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated. Silica gel chromatography using 30-100% DCM-heptane yields the title compound.

Workup

  1. custompurged with a continuous stream of N2 gas
  2. customIn a separate flask purged with a continuous stream of N2 gas
  3. temperaturecooled to −78° C
  4. additionwas added dropwise
  5. customquenched with saturated aqueous NH4Cl
  6. concentrationconcentrated
  7. additionWater was added
  8. extractionThe mixture was extracted with EtOAc
  9. dry with materialThe organic layers were dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d28026db8cdc490abe87464e0449a77e
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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