Methanol → HCID 123439779, compound

HRID 2202682Notes

Reaction equation

HRID 2202682 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:10]#N.CCCCCC.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=[O:28].[Na+].[K+]>C(Cl)Cl.[H-].C([Al+]CC(C)C)C(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[O:28]

Participants

7

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 9357Potassium Sodium TartrateHCID 11460001HCID 11460001, compound

Product 1

HCID 123439779HCID 123439779, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21225700DiisobutylaluminumhydrideSolvent

Procedure

To a solution of 2-(2,6-dichlorophenyl)-2-((trimethylsilyl)oxy)acetonitrile (1.372 g, 5.00 mmol) in DCM (23.16 ml), diisobutylaluminum hydride 1.0 M solution in hexane (7.50 ml, 7.50 mmol) was added at −78° C. dropwise over 20 min. Reaction was carefully quenched first with MeOH (1 ml, 24.97 mmol) and then with Rochelle salt 1.5 M (5.00 ml, 7.50 mmol). The flask was removed from the bath and allowed to reach ambient temperature and extracted with EtOAc (20 ml). The organic layer was separated and washed with brine, filtered through celite pad and concentrated to obtain 2-(2,6-dichlorophenyl)-2-((trimethylsilyl)oxy)acetaldehyde (1.34 g, 97%) as a white solid.

Workup

  1. customReaction
  2. customThe flask was removed from the bath
  3. customto reach ambient temperature
  4. extractionextracted with EtOAc (20 ml)
  5. customThe organic layer was separated
  6. washwashed with brine
  7. filtrationfiltered through celite pad
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d2d537d8cfa1439ea845ff435f3048c7
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

Loading…