Ethyl Acetate → N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide

HRID 594381노트

반응식

HRID 594381 반응식
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=O.[CH3:16][C:17]([S:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[N:22][S:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 220843Dibenzo(b,d)furan-2-carboxaldehydeHCID 3382465Tert-Butanesulfinamide

생성물 1

HCID 86695630N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of commercially available dibenzo[b,d]furan-2-carbaldehyde (1.992 g; 10.20 mmol), titanium(IV) ethoxide Ti(OEt)4 (3.98 ml; 19.00 mmol), and 2-methylpropane-2-sulfinamide (1.150 g; 9.49 mmol) in anh. THF (18 ml) was stirred at rt, under nitrogen, for 4 h. AcOEt and brine were added, and the organic layer was further washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM) afforded N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide as a pale yellow solid. LC-MS (conditions A): tR=0.96 min.; [M+H]+: 300.33 g/mol.

후처리

  1. washthe organic layer was further washed with brine
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by FC (DCM)

출처 및 근거

ORD 기록
ord-52acc40b5af041ff86e04ebb99c8d6e1
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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