Methyl 4-(chloromethyl)benzoate → HCID 70102981, compound

HRID 1939381Notes

Reaction equation

HRID 1939381 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.[CH3:22][O:23][C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1)=[O:25]>>[OH:1][CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[N:15]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][CH:28]=2)[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1

Participants

3

Reactant 2

HCID 36664Methyl 4-(chloromethyl)benzoateHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 70102981HCID 70102981, compoundYield 65%

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by methods F and G, alkylating with 4-(methoxycarbonyl)benzyl chloride, to afford the alcohol as a white solid in 65% yield, mp=94°-95° C.; 1H NMR (CDCl3) δ8.00 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 6.95-7.04 (m, 2H), 6.89 (dt, J=2.1, 8.0 Hz, 1H), 6.77 (dd, J=7.8, 1.5 Hz, 1H), 5.20 (s, 2H), 4.86 (dd, J=5.4, 7.7 Hz, 1H), 3.82-3.96 (m, 5H with 3H singlet at δ3.89), 2.16-2.37 (m, 3H, one of which is exchangeable). 13C NMR (CDCl3) δ166.8, 166.5, 144.1, 141.1, 130.1 (CH), 129.4, 128.4, 126.3 (CH), 124.2 (OH), 122.8 (OH), 117.3 (OH), 115.2 (OH), 75.1 (OH), 58.7 (OH2), 52.0 (CH3), 45.1 (CH2), 33.1 (CH2). IR 3450-3500 (br), 1719, 1660 cm-1. MS 342 (MH+), 324 (M-OH)+, 310 (M-OMe)+. Anal. Calc'd. for C19H19NO5 : C, 66.85; H, 5.61; N, 4.10. Found: C, 66.48; H, 5.47; N, 3.97.

Sources & evidence

ORD record
ord-ca86d7ce4a484c7e94cefd5666c5bf0c
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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