Triethylamine → 5-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole

HRID 842100

반응식

HRID 842100 반응식
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1.[CH3:19][CH:20]([OH:23])[C:21]#[CH:22].C(N(CC)CC)C>C1(C)C=CC=CC=1.[Cu]I>[Cl:18][C:4]1[CH:3]=[C:2]([C:22]#[C:21][CH:20]([OH:23])[CH3:19])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 46392547-Bromo-5-chloro-2-(2-chlorophenyl)-1,3-benzoxazole

생성물 1

HCID 46392555-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매

실험 절차

15.98 g (46.6 mmol) of 7-bromo-5-chloro-2-(2-chlorophenyl)-benzoxazole and 5 5.48 ml (69.9 mmol) of (±)-3-butyn-2-ol were heated for 6 h at 90-5° C. in 47 ml of toluene with 47 ml of triethylamine, 163.5 mg (233 μmol) of bis-triphenylphosphine-palladium(II)-dichloride and 8.9 mg (46.6 23 μmol) of copper(I) iodide. The reaction was filtered and the solid washed with toluene. The filtrate was evaporated in vacuo to dryness, the residue taken up in 150 ml of dichloromethane, extracted twice with 50 ml of 1 N HCl, dried with sodium sulfate, and filtered through 120 g of silica gel in a column. The title compound (11.11 g) was recovered as an off-white solid. A recrystallized sample from di-isopropyl ether had mp 129-31° C.

후처리

  1. filtrationThe reaction was filtered
  2. washthe solid washed with toluene
  3. customThe filtrate was evaporated in vacuo to dryness
  4. extractionextracted twice with 50 ml of 1 N HCl
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered through 120 g of silica gel in a column
  7. customThe title compound (11.11 g) was recovered as an off-white solid

출처 및 근거

ORD 기록
ord-67031ac3d51842e2b56c7159d7e2d5c1
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372770B1

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