Lithium hydroxide, monohydrate → 1,3-Dicarboxybicyclo[3.2.1]octane

HRID 1175829노트

반응식

HRID 1175829 반응식
[C:1]([C:5]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][CH:7]([C:13]([O:15]C)=[O:14])[CH2:6]2)([O:3]C)=[O:2].O.[OH-].[Li+]>O1CCCC1.C(O)(C)C.O>[C:1]([C:5]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][CH:7]([C:13]([OH:15])=[O:14])[CH2:6]2)([OH:3])=[O:2]

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 684229871,3-Dicarbomethoxybicyclo[3.2.1]octane

생성물 1

HCID 684249611,3-Dicarboxybicyclo[3.2.1]octane수율 86.4%

시약·촉매·용매 3

HCID 962Water용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A stirred solution of 1,3-dicarbomethoxybicyclo[3.2.1]octane (8.26 g, 36.5 mmol) in tetrahydrofuran (50 mL) and isopropanol (16 mL) was treated with a solution of lithium hydroxide hydrate (4.20 g, 100 mmol) in water (50 mL), and the mixture was heated to 60°-70° C. for 2 h with stirring. The organic solvents were removed in vacuo, and the alkaline aqueous solution was cooled on an ice bath and acidified with concentrated hydrochloric acid (10 mL). The solid was filtered, rinsed with cold water, and partially air dried overnight, then further dried under vacuum, triturated from acetonitrile, and redried in vacuo to afford 6.25 g (86%) of subject material as a white solid. No MS could be obtained. 1H NMR (CDCl3+drop d6-DMSO) δ 2.15-2.25 (m, 1H), 1.95-2.05 (m, 2H), 1.40-1.70 (m, 9H).

후처리

  1. temperaturethe mixture was heated to 60°-70° C. for 2 h
  2. customThe organic solvents were removed in vacuo
  3. temperaturethe alkaline aqueous solution was cooled on an ice bath
  4. filtrationThe solid was filtered
  5. washrinsed with cold water, and partially air
  6. customdried overnight
  7. customfurther dried under vacuum
  8. customtriturated from acetonitrile
  9. customredried in vacuo

출처 및 근거

ORD 기록
ord-88678b9f8592420c8511ba65c6cddb25
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842707B2

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