Hydrochloric Acid → 4,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranone

HRID 925060노트

반응식

HRID 925060 반응식
[C:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C:2]=1[CH2:3][CH2:4][CH2:5][CH2:6]2.[BH4-].[Na+].Cl>O1CCCC1>[OH:11][CH:10]1[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[C:7](=[O:8])[O:9]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 4311764Sodium borohydride

생성물 1

HCID 109097774,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-cyclohexene-1,2-dicarboxylic anhydride (25.2 g) in tetrahydrofuran (125 mL) at 0° C. was added sodium borohydride (1.51 g). The mixture was warmed to ambient temperature for 30 minutes, heated at reflux for 5 hours, cooled, treated with 1N hydrochloric acid and concentrated. The concentrate was partitioned between ethyl acetate and brine, and the organic layer was washed with brine and water and concentrated. The concentrate was purified by flash chromatography with 50% ethyl acetate in hexane.

후처리

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe concentrate was partitioned between ethyl acetate and brine
  6. washthe organic layer was washed with brine and water
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash chromatography with 50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-21ad948c0b8e4a9facb190b2bce48c6e
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283222B2

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