Water → HCID 18008065, compound

HRID 2117230Notes

Reaction equation

HRID 2117230 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][O:13][CH2:14][CH2:15][CH2:16][OH:17])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:21][C:22]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:23]=1[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25].O>CN1C(=O)N(C)CCC1.C1COCC1>[CH3:21][C:22]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][O:17][CH2:16][CH2:15][CH2:14][O:13][CH2:12][C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH:9]=2)[C:23]=1[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22241269HCID 22241269, compoundHCID 22256028HCID 22256028, compound

Product 1

HCID 18008065HCID 18008065, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
0 °C

Procedure

3-(2-Phenyl-oxazol-4-ylmethoxy)-propan-1-ol (1.26 g, 5.4 mmol) is dissolved in 10% DMPU in THF (20 mL) and cooled to 0° C. Sodium hydride (60%, 237 mg, 5.9 mmol) is added portionwise. The contents are stirred for 10 min. at 0° C., warmed to r.t. and stirred for another 10 min. isobutyl 2-bromomethyl-6-methyl-benzoate (2.69 g, 5.4 mmol, EXAMPLE 2b) is added, allowed to come to r.t. and stirred overnight. The reaction is poured into water (200 mL) and extracted with ethyl acetate (2×200 mL). The organic fractions were pooled and washed with brine (2×200 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material was purified by flash chromatography (silica, 15-20% ethyl acetate in hexane) to give the title compound (1.06 g). MS (ESI) 438 (M+H)+.

Workup

  1. temperaturewarmed to r.t.
  2. additionis added
  3. customto come to r.t.
  4. stirringstirred overnight
  5. extractionextracted with ethyl acetate (2×200 mL)
  6. washwashed with brine (2×200 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customThe crude material was purified by flash chromatography (silica, 15-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-69b16b107dd74ea8b712f7053ab7dc8d
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

Loading…