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

HRID 925060ノート

反応式

HRID 925060 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-21ad948c0b8e4a9facb190b2bce48c6e
出典データセット
uspto-grants-2016_03
特許番号
US09283222B2

反応ノート

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