tert-Butanol → HCID 131725687, compound

HRID 1794656Notes

Reaction equation

HRID 1794656 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C-:10]#[N:11].[K+].C(O)(C)(C)C.[C:18]([O:21]C(=O)C)(=[O:20])[CH3:19]>C(Cl)Cl.[Ti]>[C:18]([OH:21])(=[O:20])[CH3:19].[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[C:10]#[N:11]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 69962-ChlorobenzaldehydeHCID 7918Acetic AnhydrideHCID 9032Potassium Cyanide

Product 1

HCID 131725687HCID 131725687, compound

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 6344DichloromethaneSolvent

Procedure

o-Chlorobenzaldehyde (1.0 g, 0.82 ml, 7.11 mmol) was added via syringe to an agitated mixture of potassium cyanide (1.85 g, 28.46 mmol) and a titanium dimer catalyst of Formula (8) (72.8 mg, 0.06 mmol) in CH2Cl2 (18 ml), followed by t-butanol (0.56 g, 0.72 ml, 7.49 mmol). The slurry was cooled to a temperature of −5° C. and acetic anhydride (2.905 g, 2.68 ml, 28.46 mmol) was added via a syringe. The slurry was agitated at a temperature of −5° C. to 0° C. Analysis by G.C. showed that the reaction had gone to 31% conversion (49% e.e.) after 4 hrs and to 33% conversion (51% e.e.) after 5.75 hrs.

Workup

  1. additionwas added via a syringe

Sources & evidence

ORD record
ord-bab87a965cd844b3bfed32958ba09054
Source dataset
uspto-grants-2006_04
Patent number
US07022876B2

Reaction notes

Loading…