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

HRID 2299757ノート

反応式

HRID 2299757 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-74e0f4d2cbb247b1acaad156cbddc537
出典データセット
uspto-grants-2002_12
特許番号
US06495581B1

反応ノート

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