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Lithium Hydroxide → ({[2-(4-Chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid

HRID 254099
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HRID 254099 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][S:17][CH2:18][C:19]([O:21]CC)=[O:20])[O:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][S:17][CH2:18][C:19]([OH:21])=[O:20])[O:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][O:13]2)=[CH:4][CH:3]=1
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5

반응물 2

HCID 3939Lithium HydroxideHCID 86619094Ethyl ({[2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

생성물 1

HCID 66843234({[2-(4-Chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid수율 96.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Ethyl ({[2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate (3.36 g, 9.36 mmol) was dissolved in THF (45 ml) and cooled to 0° C. LiOH (0.79 g, 18.8 mmol) in water (12 ml) was added and the mixture was stirred for 18 h at room temperature. The solvents were evaporated. The crude product was extracted between water and diethyl ether. The aqueous layer was acidified using 2M HCl to pH 6 and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to afford 2.98 g (96%) of the title compound as an yellow oil. 1H-NMR (CDCl3, 300 MHz): δ 0.62 (s, 3H), 1.34 (s, 3H), 2.95 (s, 2H), 3.34 (s, 2H), 3.45 (s, 4H), 7.4 (m, 4H)

후처리

  1. customThe solvents were evaporated
  2. extractionThe crude product was extracted between water and diethyl ether
  3. extractionextracted twice with CH2Cl2
  4. dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6a342756751c4f76ac2a7409eb507e0b
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07871998B2

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