Hydrochloric Acid → 1-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol

HRID 496863노트

반응식

HRID 496863 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:27]=[CH:26][C:11]([C:12]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][C:15]=2[C:23](O)=[O:24])=O)=[CH:10][CH:9]=1.Cl>C1COCC1>[F:7][C:8]1[CH:27]=[CH:26][C:11]([CH:12]2[C:14]3[C:15](=[CH:16][C:17]([CH2:18][OH:19])=[CH:21][CH:22]=3)[CH2:23][O:24]2)=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 98355864-(4-Fluorobenzoyl)isophthalic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 99211661-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol수율 8.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of lithium aluminum hydride (1.0 g) dispersed in THF (10 ml) was added dropwise at room temperature a solution of 4-(4′-fluorobenzoyl)isophthalic acid (3.0 g) in THF (30 ml), and the mixture was stirred for 10 hr. To the reduced reaction mixture was added 10% hydrochloric acid (10 ml) and the mixture was passed through celite. THF was evaporated under reduced pressure, and 85% phosphoric acid (10 g) was added. The mixture was stirred at 60° C. for 5 hr. To the reaction mixture was added water (50 ml) and the resulting crystals were collected by filtration and dried. The objective compound was separated by silica gel column chromatography to give 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol (0.21 g, 8%). The various spectrum data of the crystals were the same as those obtained in Example 12.

후처리

  1. customTHF was evaporated under reduced pressure, and 85% phosphoric acid (10 g)
  2. additionwas added
  3. stirringThe mixture was stirred at 60° C. for 5 hr
  4. additionTo the reaction mixture was added water (50 ml)
  5. filtrationthe resulting crystals were collected by filtration
  6. customdried
  7. customThe objective compound was separated by silica gel column chromatography

출처 및 근거

ORD 기록
ord-97755c0207c144f29d98d69a036f6273
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06946564B2

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