Dimethylformamide dimethyl acetal → HCID 58059659, compound

HRID 1842569Notes

Reaction equation

HRID 1842569 reaction equation
[Si:1]([O:8][CH:9]([CH:23]([CH3:25])[CH3:24])[C:10](=[O:22])[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>C1(C)C=CC=CC=1>[Si:1]([O:8][CH:9]([CH:23]([CH3:25])[CH3:24])[C:10](=[O:22])/[C:11](=[CH:28]/[N:29]([CH3:31])[CH3:30])/[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 58059648HCID 58059648, compound

Product 1

HCID 58059659HCID 58059659, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of benzyl 4-{[tert-butyl(dimethyl)silyl]oxy}-5-methyl-3-oxohexanoate (0.39 g, 1.06 mmol) in toluene (5.3 mL) were added 1,1-dimethoxy-N,N-dimethylmethanamine (0.21 mL, 1.59 mmol). The mixture was heated to 110° C. After 18 h, excess amount of 1,1-dimethoxy-N,N-dimethylmethanamine was added and the mixture was concentrated. Purification by silica gel chromatography (75% hexanes/ethyl acetate 25% hexanes/ethyl acetate) gave the title compound (0.133 g).

Workup

  1. concentrationthe mixture was concentrated
  2. customPurification by silica gel chromatography (75% hexanes/ethyl acetate 25% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-001f6d0f4955493bb36f35ca96020df8
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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