Sodium hydride → 2-({[4-(Benzyloxy)benzyl]oxy}methyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole

HRID 2066642Notes

Reaction equation

HRID 2066642 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][O:14][CH2:15][C:16]([CH3:28])([OH:27])[CH2:17][N:18]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[N:20]=[C:19]2Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][O:14][CH2:15][C:16]2([CH3:28])[O:27][C:19]3=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:18]3[CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 669560821-{[4-(benzyloxy)benzyl]oxy}-3-(2-bromo-4-nitro-1H-imidazol-1-yl)-2-methyl-2-propanol

Product 1

HCID 509136332-({[4-(Benzyloxy)benzyl]oxy}methyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazoleYield 97%

Procedure

Ring closure of alcohol 126 with NaH (1.5 equiv.) as in Example 2A for 80 min, followed by chromatography of the product on silica gel, eluting with CH2Cl2, gave 26 (97%) as a cream solid: mp (CH2Cl2/hexane) 130-131° C.; 1H NMR (CDCl3) δ 7.48 (s, 1H), 7.45-7.29 (m, 5H), 7.16 (dt, J=8.7, 2.4 Hz, 2H), 6.94 (dt, J=8.7, 2.4 Hz, 2H), 5.06 (s, 2H), 4.52 (d, J=11.7 Hz, 1H), 4.47 (d, J=11.7 Hz, 1H), 4.32 (d, J=10.0 Hz, 1H), 3.86 (d, J=10.0 Hz, 1H), 3.67 (d, J=10.6 Hz, 1H), 3.53 (d, J=10.6 Hz, 1H), 1.62 (s, 3H). Anal. (C21H21N3O5) C, H, N.

Workup

  1. customfor 80 min
  2. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-1b1ce8a13836494cbe3fc1e5c9f6f5fb
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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