Sodium hydride → 2-[3-(Methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole

HRID 7713

Reaction equation

HRID 7713 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([CH3:17])=[C:14]([OH:16])[CH:15]=1.[H-].[Na+].Br[CH2:21][O:22][CH2:23]Br>C1COCC1>[CH3:21][O:22][CH2:23][O:16][C:14]1[CH:15]=[C:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[CH:11]=[CH:12][C:13]=1[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13349653Bromo(bromomethoxy)methaneHCID 219910005-(1,3-Benzoxazol-2-yl)-2-methylphenol

Product 1

HCID 219910022-[3-(Methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (200 mg, 0.89 mmol) in THF (6 mL) was cooled to −78° C. under Argon and sodium hydride (24 mg, 1.0 mmol) was added. After 30 min at this temperature, bromomethyl ether (225 mg, 1.8 mmol) was added via syringe. The reaction was warmed to rt for 1 h. The reaction mixture was concentrated and the residue was purified by flash column (silica gel, hexanes:EtOAc 4:1) to afford 2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole. MS (ESI) 270 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash column (silica gel, hexanes:EtOAc 4:1)

Sources & evidence

ORD record
ord-aa5a2b97ad7343c18a3533749cd3c636
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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