1-Chloropentane → HCID 54315516, compound

HRID 1459617Notes

Reaction equation

HRID 1459617 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.Cl[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[K+].[Br-]>>[OH:1][CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[N:15]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1

Participants

4

Reactant 3

HCID 109771-ChloropentaneHCID 253877Potassium BromideHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 54315516HCID 54315516, compoundYield 32%

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 1-chloropentane in 32% yield and isolated as a colorless oil; IR (KBr) 3424, 2956, 2932, 1680, 1500, 1272, 1062, 749 cm-1 ; 1H NMR (CDCl3) δ 0.91 (t, J=6.8 Hz, 3H), 1.31-1.38 (m, 4H), 1.66 (br t, J=5.5 Hz, 2H), 2.08-2.29 (m, 2H), 2.59 (br s, 1H), 3.87-3.94 (m, 2H), 4.69 (dd, J=7.3, 5.8 Hz, 1H), 6.92-7.08 (m, 4H); Anal. Calc'd for C15H21NO3 : C, 68.42; H, 8.04; N, 5.32. Found: C, 68.10; H, 7.88; N, 5.32.

Workup

  1. customisolated as a colorless oil

Sources & evidence

ORD record
ord-0a585b5c407d49dfbc25c742c83a83bf
Source dataset
uspto-grants-1998_12
Patent number
US05854242

Reaction notes

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