Dimethylformamide → 4,4-Dimethylchroman-8-carbaldehyde

HRID 22988Notes

Reaction equation

HRID 22988 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[C:7](I)[CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.C([Li])CCC.CN([CH:22]=[O:23])C.[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[C:7]([CH:22]=[O:23])[CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 225926494,4-Dimethyl-8-iodochromanHCID 178418339Butyllithium

Product 1

HCID 225926624,4-Dimethylchroman-8-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14.40 g (50.0 mmol) of 4,4-dimethyl-8-iodochroman and 50 ml of THF are introduced into a three-necked flask under a stream of nitrogen. 22 ml (55.0 mmol) of n-butyllithium (2.5M in hexane) are added dropwise at −78° C., the reaction mixture is stirred for 30 minutes, then 4.2 ml (55.0 mmol) of DMF are added and the mixture is allowed to return to room temperature. The reaction mixture is poured onto an aqueous ammonium chloride solution and extracted with ethyl ether and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. 10.40 g (100%) of the expected compound are collected in the form of a yellow oil.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom10.40 g (100%) of the expected compound are collected in the form of a yellow oil

Sources & evidence

ORD record
ord-bc3f6087b2244158870fc5f9471c7fa8
Source dataset
uspto-grants-2005_02
Patent number
US06849658B2

Reaction notes

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