Dichloromethane → HCID 178472872, compound

HRID 1194905Notes

Reaction equation

HRID 1194905 reaction equation
Br[C:2]([CH:5]1[CH2:10][CH2:9][CH:8]([CH3:11])[CH2:7][CH2:6]1)([CH3:4])[CH3:3].[OH:12]/[N:13]=[C:14](/[C:20](=[O:22])[CH3:21])\[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(Cl)Cl>O1CCOCC1.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:2]([CH3:4])([O:12]/[N:13]=[C:14](/[C:20](=[O:22])[CH3:21])\[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:3])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 21248920HCID 21248920, compoundHCID 178472876HCID 178472876, compound

Product 1

HCID 178472872HCID 178472872, compound

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-2-(4-methylcyclohex-1-yl)propane (1.99 g, 9.06 mmol), ethyl (Z)-2-hydroxyimino-3-oxobutyrate (1.44 g, 9.06 mmol) and silver trifluoromethanesulphonate (2.33 g) were reacted together in dry dioxane (8 ml) using a similar method to Example 9a. The title compound was obtained as an oil (1.31 g, 51%), νmax (CH2Cl2) 2920, 2860, 1740, 1685, 1370, 1320, 1235, 1070, and 1000 cm-1. δ13C (100 MHz, CDCl3) 14.14 (CH3), 22.55 (CH3), 23.24 (2×CH3), 25.11 (CH3), 26.8 (2×CH2), 32.76 (CH), 35.36 (2×CH2), 46.25 (CH), 61.7 (CH2) 87.6, 149.7, 161.6 (C=O), 193.1 (C=O); δH (400 MHz, CDCl3), 0.86 (3H, d, J 6.5 Hz), 0.8-0.95 (2H, m), 0.95-1.15 (2H, m), 1.29 (6H, s), 1.32 (3H, t, J 7.1 Hz), 1.2-1.35 (1H, m), 1.45-1.65 (2H, m), 1.65-1.80 (3H, m), 2.40 (3H, s), and 4.34 (2H, q, J 7.1 Hz).

Sources & evidence

ORD record
ord-c87a8bd633d34390b2ec00c3247a3f13
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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