Sodium Hydroxide → 2-(6-Fluoro-1-hydroxy-1-indanyl)acetic acid

HRID 862757노트

반응식

HRID 862757 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:12][C:13]([O:15]CC)=[O:14])[OH:11])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:12][C:13]([OH:15])=[O:14])[OH:11])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 23293626Ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

생성물 1

HCID 232935722-(6-Fluoro-1-hydroxy-1-indanyl)acetic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate (44.0 g, 0.18 mol), 1N sodium hydroxide (180 mL) and absolute ethanol (280 mL) was stirred for 18 h at room temperature. The mixture was concentrated in vacuo, diluted with H2O and extracted with diethyl ether. The aqueous phase was acidified (pH 3) with dilute hydrochloric acid and extracted with diethyl ether. The diethyl ether layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 2-(6-fluoro-1-hydroxy-1-indanyl)acetic acid as an amber oil (37.7 g, 100%; Note: This compound spontaneously dehydrated upon standing at room temperature to a mixture of olefins unless immediately reacted with trifluoroacetic acid); NMR (DMSO-d6): d 11.60 (br s, 1H, COOH), 6.75-7.05 (m, 3H, Ar), 5.20 (br s, 1H, OH), 2.22-2.69, 1.77-1.95 (2m's, 6H, 3XCH2).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with H2O
  3. extractionextracted with diethyl ether
  4. extractionextracted with diethyl ether
  5. washThe diethyl ether layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-731223b290c84fbea659aedf1a8299cf
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719186

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