Benzyl Bromide → HCID 86608891, compound

HRID 1992575Notes

Reaction equation

HRID 1992575 reaction equation
[OH:1][C:2]1[C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[CH:3]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:25]COC(C)=O>>[CH2:17]([O:1][C:2]1[C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[C:3]=1[CH3:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 1355380184-hydroxy-5-Methyl-5-octylthiophen-2(5H)-one

Product 1

HCID 86608891HCID 86608891, compoundYield 75%

Procedure

To 32 (50 mg, 0.21 mmol) and benzyl bromide (37 mL, 0.31 mmol) following General Procedure H, was obtained 76 (49 mg, 75%) after flash chromatography (15% EtOAc/Hex). 1H NMR (300 MHz, CDCl3) δ 0.86 (t, J=6.9 Hz, 3H), 1.24 (m, 11H), 1.41-1.48 (m, 1H), 1.66 (s, 3H), 1.79-1.86 (m, 2H), 4.98 (s, 2 H), 5.39 (s, 1H), 7.31-7.42 (m, 5H); 13C NMR (100 MHz, CDCl3) δ 14.1, 22.6, 25.0, 26.4, 29.1, 29.3, 29.4, 31.8, 38.8, 59.7, 74.0, 102.2, 127.6, 128.8, 128.8, 134.3, 185.8, 194.1. IR (NaCl) 2928, 1681, 1610 cm−1.

Sources & evidence

ORD record
ord-06a828f6e7fc4a7d97182ac2d16ff72c
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

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