Water → HCID 22507779, compound

HRID 985727Notes

Reaction equation

HRID 985727 reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.[Si](C=[N+]=[N-])(C)(C)C.[Cl:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.O>C1COCC1>[C:25]([C:24]1[CH:27]=[CH:28][C:21]([O:20][CH2:19][CH2:18][CH2:17][Cl:16])=[CH:22][CH:23]=1)#[CH:2]

Participants

6

Reactant 4

HCID 962WaterHCID 167693TrimethylsilyldiazomethaneHCID 2724682Lithium diisopropylamideHCID 35514794-(3-Chloropropoxy)-benzaldehyde

Product 1

HCID 22507779HCID 22507779, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To LDA (2M in THF, 15 mL) in THF (100 mL) at −78° C., TMSCHN2 (2M in hexanes, 15 mL) was added dropwisely. Ten minutes later, 4-(3-chloropropoxy)benzaldehyde (0.025 mol, 4.97 g) in THF (60 mL) was added. After 1 h stirring at −78° C., the mixture was warmed up and refluxed for 3 h. Water (250 mL) was added and extracted by EtOAc (2×200 mL). After being dried over Na2SO4 and concentration, the title compound (4.8 g) was obtained.

Workup

  1. temperaturethe mixture was warmed up
  2. temperaturerefluxed for 3 h
  3. extractionextracted by EtOAc (2×200 mL)
  4. dry with materialAfter being dried over Na2SO4 and concentration

Sources & evidence

ORD record
ord-6be62ff32905469c90ace6d853ea2008
Source dataset
uspto-grants-2005_03
Patent number
US06872834B2

Reaction notes

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