tert-Butyl bromoacetate → HCID 131720598, compound

HRID 1598818Notes

Reaction equation

HRID 1598818 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=1)[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20]2)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31]([O:35][C:36](=[O:39])[CH2:37]Br)([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=1)[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([O:27][CH2:37][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:39])[CH:21]=[CH:20]2)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 18930715HCID 18930715, compound

Product 1

HCID 131720598HCID 131720598, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxynaphthalene 330e (0.60 g, 1.5 mmol) was alkylated with t-butylbromoacetate (0.24 mL, 1.5 mmol) in the presence of K2 CO3 (0.20 g, 1.5 mmol) in DMF (7 mL) in the usual way to yield a colorless solid (0.64 g) after silica gel chromatography. IR(KBr): cm-1 3340, 1746, 1684. 1H NMR(300 MHz, CDCl3): 8.21 (s, 1H), 7.94-7.10 (m, 9H), 5.0 (br, 1H), 4.68 (s, 2H), 4.09 (t, 2H, J=7 Hz), 3.56-3.52 m, 2H), 1.52 (s, 9H), 1.44 (2, 9H). MS(NH3): 539 (base, M+NH4), 522 (25%, M+H).

Sources & evidence

ORD record
ord-1025f0c6acd644bb885f2e4ffee64245
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

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