Monobenzone → HCID 66956632, compound

HRID 2066653Notes

Reaction equation

HRID 2066653 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C:12]2([CH3:15])[CH2:14][O:13]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:14][C:12]([CH3:15])([OH:13])[CH2:11][CH2:10][N:3]2[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]2[Cl:1])=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 7638MonobenzoneHCID 86650547HCID 86650547, compound

Product 1

HCID 66956632HCID 66956632, compoundYield 79%

Procedure

Reaction of epoxide 140 (see Example 2JJ) with 4-(benzyloxy)phenol as in Example 2AA at 82° C. for 10 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 2% EtOAc/CH2Cl2, gave 1-[4-(benzyloxy)phenoxy]-4-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-2-butanol (142) (79%) as an oil; 1H NMR (CDCl3) δ 7.79 (s, 1H), 7.44-7.29 (m, 5H), 6.92 (dt, J=9.2, 3.0 Hz, 2H), 6.83 (dt, J=9.2, 3.0 Hz, 2H), 4.28 (ddd, J=14.0, 9.7, 6.1 Hz, 1H), 4.23 (ddd, J=14.0, 9.7, 6.3 Hz, 1H), 3.81 (d, J=9.1 Hz, 1H), 3.77 (d, J=9.0 Hz, 1H), 2.29 (s, 1H), 2.22 (ddd, J=13.8, 9.6, 6.2 Hz, 1H), 2.02 (ddd, J=13.6, 9.7, 6.5 Hz, 1H), 1.38 (s, 3H); HRESIMS calcd for C21H23ClN3O5 m/z [M+H]+ 434.1293, 432.1321. found 434.1298, 432.1319.

Workup

  1. customat 82° C.
  2. customfor 10 h
  3. washeluting with CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-f971482022ed45018eeeb7303fe68549
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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