Dimethylformamide → 1H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-

HRID 1593416Notes

Reaction equation

HRID 1593416 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.C([Li])CCC.CN(C)[CH:21]=[O:22]>O1CCCC1>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:21]=[O:22])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 730128401H-Inden-1-one, 5-bromo-2,3-dihydro-, O-methyloximeHCID 178418339Butyllithium

Product 1

HCID 730123441H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

A solution of the product of Step 1 (112 g, 0.46 mol) in tetrahydrofuran (1500 ml) at −60° C. under argon, was treated with n-butyllithium (325 ml of a 1.6M solution in hexanes, 0.52 mol) over 1 hour. After stirring at −60° C. for 1 hour a solution of dimethylformamide (39.7 ml) in tetrahydrofuran (50 ml) was added dropwise over 1 hour. The reaction was stirred at −60° C. for 1 hour before being allowed to warm to room temperature. After 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted into ethyl acetate.

Workup

  1. additionwas added dropwise over 1 hour
  2. temperatureto warm to room temperature
  3. customAfter 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution
  4. extractionextracted into ethyl acetate

Sources & evidence

ORD record
ord-c1a3562d4f0046feac376cc18e25cff4
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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