Diisobutylaluminum hydride → 2-Methyl-2-(4-methylsulphonylphenoxy)propanal

HRID 344733Notes

Reaction equation

HRID 344733 reaction equation
CC(OC1C=CC(SC)=CC=1)(C)C(OCC)=O.ClC1C=CC=C(C(OO)=O)C=1.[CH3:29][C:30]([O:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([CH3:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1)([CH3:36])[C:31](OCC)=[O:32].CC(C[AlH]CC(C)C)C>ClCCl>[CH3:36][C:30]([O:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([CH3:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1)([CH3:29])[CH:31]=[O:32]

Participants

6

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 70297m-Chloroperbenzoic acidHCID 19895624Ethyl 2-methyl-2-(4-(methylthio)phenoxy)propionateHCID 54111087Ethyl 2-methyl-2-(4-methylsulphonylphenoxy)propionate

Product 1

HCID 151920502-Methyl-2-(4-methylsulphonylphenoxy)propanalYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The necessary aldehyde was obtained by an analogous procedure to that described in connection with Example 19 starting from 4-(methylthio)phenol which was converted to ethyl 2-methyl-2-(4-(methylthio)phenoxy)propionate [oil, 20% yield; NMR: 1.25(3H,t J=7 Hz), 1.6(6H,s), 2.45(3H,s), 4.25(2H,q J=7 Hz), 6.75-7.2(4H,m)]. This ester was oxidised with m-chloroperbenzoic acid in dichloromethane at ambient temperature to give, after conventional work-up, ethyl 2-methyl-2-(4-methylsulphonylphenoxy)propionate [oil, slowly solidifying: 92% yield; NMR: 1.25(3H,q J=7 Hz), 1.65(6H,s), 3.0(3H,s), 4.25(2H,q J=7 Hz), 6.9-6.95(2H,m), 7.8-7.85(2H,m)] which was then reduced with DIBAL to give 2-methyl-2-(4-methylsulphonylphenoxy)propanal as a solid (66% yield); NMR: 1.5(6H,s), 3.05(3H,s), 6.9-7.0(2H,m), 7.8-7.9 (2H,m), 9.8(1H,s).

Workup

  1. customto give

Sources & evidence

ORD record
ord-9568274366fd43ce8836b22ff0df84af
Source dataset
uspto-grants-1991_10
Patent number
US05053415

Reaction notes

Loading…