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Ethanol → Methyl 3-(4-{[4-(hydroxymethyl)phenoxy]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate

HRID 2221585
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HRID 2221585 반응식
[CH:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([O:20][CH3:21])=[O:19])[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1)=[O:2].C(O)C.[BH4-].[Na+].O>O1CCCC1>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([O:20][CH3:21])=[O:19])[O:12][C:13]=2[CH3:14])=[CH:25][CH:26]=1
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참가 물질

6

반응물 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86605721Methyl 3-{4-[(4-formylphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate

생성물 1

HCID 23076400Methyl 3-(4-{[4-(hydroxymethyl)phenoxy]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate수율 91%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of methyl 3-{4-[(4-formylphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate (2.12 g) in tetrahydrofuran (30 mL)-ethanol (5 mL) was gradually added sodium borohydride (0.23 g) at room temperature. After stirring the reaction mixture at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give methyl 3-(4-{[4-(hydroxymethyl)phenoxy]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate as colorless crystals (1.93 g, yield 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 105-106° C.

후처리

  1. customat room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af806c8bea394b558340f8c193c6cd2e
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07368578B2

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