Dimethylformamide → 3-[2-(Tetrahydropyran-2-yloxy)-ethyl]-benzaldehyde

HRID 1435571Notes

Reaction equation

HRID 1435571 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CCCCCC.CN(C)[CH:30]=[O:31]>C1COCC1.ClCCl.O>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[O:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:30]=[O:31]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 184035082-(3-bromophenethoxy)tetrahydro-2H-pyranHCID 178418339Butyllithium

Product 1

HCID 866183253-[2-(Tetrahydropyran-2-yloxy)-ethyl]-benzaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.14 g (7.52 mmol) 2-[2-(3-Bromo-phenyl)-ethoxy]-tetrahydro-pyran in 9 ml dry THF were cooled to −78 C and treated dropwise with 9.87 ml of 1.6M solution of butyl lithium in hexane (15.79 mmol). After stirring for 30 min, 2.31 g (31.58 mmol) N,N-dimethylformamide were added dropwise and stirring was continued for another 15 min at −78 C. The mixture was slowly warmed to room temperature and stirred for and another 60 min. Water and dichloromethane were added, the organic phase separated, and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried, evaporated and the residue purified by chromatography on silica in ethyl acetate heptane mixtures. Yield 1.66 g of the title compound as a pale yellow oil.

Workup

  1. stirringstirring
  2. waitwas continued for another 15 min at −78 C
  3. stirringstirred for and another 60 min
  4. customthe organic phase separated
  5. extractionthe aqueous phase extracted several times with dichloromethane
  6. customThe combined organic phases were dried
  7. customevaporated
  8. customthe residue purified by chromatography on silica in ethyl acetate heptane mixtures

Sources & evidence

ORD record
ord-64175fd6c8b44828adad42ca319ac6b3
Source dataset
uspto-grants-2009_11
Patent number
US07618964B2

Reaction notes

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