tert-Butanol → Tert-butyl 4-cyanobenzoate

HRID 979774ノート

反応式

HRID 979774 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].[C:12](O)([CH3:15])([CH3:14])[CH3:13].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8])=[CH:5][CH:4]=1)#[N:2]

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 120874-Cyanobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 271408Tert-butyl 4-cyanobenzoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

Dissolve 22.1 g 4-cyanobenzoic acid and 28.2 ml t-butanol in 500 ml DMF. Add 9.15 g 4-(dimethylamino) pyridine and 31.5 g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. Stir the mixture overnight at RT. Remove the DMF in vacuo, and partition the resultant residue between ethyl acetate and water. Wash the organic layer successively with cold 0.5 N aqueous HCl, water, 5% aqueous NaHC03 and brine. Dry the organic layer over MgSO4 and evaporate the solvent to obtain the title compound. m.p. 75°-78° C. Rf (silica gel; 5% EtOAc in hexane)=0.3; IR 2240 cm-1 ; 1730 cm-1.

後処理

  1. customRemove the DMF in vacuo
  2. custompartition the resultant residue between ethyl acetate and water
  3. washWash the organic layer successively with cold 0.5 N aqueous HCl, water, 5% aqueous NaHC03 and brine
  4. dry with materialDry the organic layer over MgSO4
  5. customevaporate the solvent

出典と根拠

ORDレコード
ord-3a3d30f66e2a4a77b8d2ec22ad808e8f
出典データセット
uspto-grants-1987_01
特許番号
US04634689

反応ノート

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