Toluene → 4-(4-Chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole

HRID 2299757노트

반응식

HRID 2299757 반응식
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:29][CH3:30])[C:14]=1[O:15][CH2:16][C:17]1[N:18]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:20][C:21]=1[CH3:22])[CH2:10]O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:3][CH2:10][C:9]1[CH:8]=[C:7]([O:6][CH3:5])[C:14]([O:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[C:13]([O:29][CH3:30])[CH:12]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 536741583,5-Dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

생성물 1

HCID 223446054-(4-Chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Thionyl chloride (3.62 g) was added dropwise to a stirred suspension of 3,5-dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (9.00 g) in tetrahydrofuran (50 ml)-toluene (150 ml) at 0° C. After stirring at room temperature for 3 hours, the reaction mixture was concentrated. The residual crystals were dissolved in ethyl acetate and washed with aqueous sodium bicarbonate and water. The ethyl acetate layer was separated, dried (MgSO4), and concentrated to give 4-(4-chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole as crystals. Recrystallization from acetone-hexane gave colorless needles (7.00 g, yield 74%). m.p. 118-119° C.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residual crystals were dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate and water
  4. customThe ethyl acetate layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-74e0f4d2cbb247b1acaad156cbddc537
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495581B1

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