3-(Phenylmethoxy)benzenemethanol → HCID 70102702, compound

HRID 1939377Notes

Reaction equation

HRID 1939377 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[CH2:22]([O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33][N:15]1[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16]1=[O:17])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 743413-(Phenylmethoxy)benzenemethanolHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 70102702HCID 70102702, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with the methanesulfonate ester of 3-benzyloxybenzyl alcohol, in 67% overall yield as a viscous liquid, after flash chromatography eluting with 30-100% EtOAc in hexane, IR (CHCl3) 3434, 2933, 1681, 1500, 1401, 1256, 1054, 751 cm-1 ; 1H NMR (CDCl3) δ1.77 (br s, 1H plus HDO), 2.20-2.34 (m, 2H), 3.91 (t, J=5.5 Hz, 2H), 4.82 (dd, J=7.5, 5.7 Hz, 1H), 5.02 (s, 2H), 5.11 (ABq, JAB =16.0 Hz, 2H), 6.85-7.01 (m, 7H), 7.22-7.41 (m, 6H); MH+ at m/z=390; Anal. Calc'd for C24H23NO4 : C, 74.02; H, 5.95; N, 3.60. Found: C, 73.61; H, 6.03; N, 3.55.

Workup

  1. customoverall yield as a viscous liquid
  2. washafter flash chromatography eluting with 30-100% EtOAc in hexane, IR (CHCl3) 3434, 2933, 1681, 1500, 1401, 1256, 1054, 751 cm-1

Sources & evidence

ORD record
ord-7cd55488eafa4abc9228923a3b629856
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

Loading…