Methanol → 1-(4-Hydroxy-4-methoxychroman-6-yl)cyclopropanecarboxylic acid

HRID 468297노트

반응식

HRID 468297 반응식
C[O:2][C:3]([C:5]1([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[O:14][CH2:13][CH2:12][CH2:11]3)[CH2:7][CH2:6]1)=[O:4].O[Li].[OH2:20].[CH3:21][OH:22]>O>[OH:20][C:11]1([O:22][CH3:21])[C:10]2[C:15](=[CH:16][CH:17]=[C:8]([C:5]3([C:3]([OH:2])=[O:4])[CH2:7][CH2:6]3)[CH:9]=2)[O:14][CH2:13][CH2:12]1

참가 물질

5

반응물 3

HCID 887Methanol2회HCID 168937Lithium hydroxide, monohydrateHCID 59129159methyl 1-(3,4-dihydro-2H-chromen-6-yl)cyclopropane-1-carboxylate

생성물 1

HCID 591292881-(4-Hydroxy-4-methoxychroman-6-yl)cyclopropanecarboxylic acid수율 76%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 1-chroman-6-yl-cyclopropanecarboxylic methyl ester (1.4 g, 60 mmol) in MeOH (20 mL) and water (20 mL) was added LiOH.H2O (1.0 g, 240 mmol) in portions at room temperature. The mixture was stirred overnight at room temperature before the MeOH was removed by evaporation under vacuum. Water and Et2O were added and the aqueous layer was separated, acidified with HCl and extracted with EtOAc (50 mL×3). The combined organic extracts dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-(4-Hydroxy-4-methoxychroman-6-yl)cyclopropanecarboxylic acid (1.0 g, 76%). 1H NMR (400 MHz, DMSO) δ 12.10 (br s, 1H), 6.95 (d, J=2.4 Hz, 2H), 6.61-6.59 (m, 1H), 4.09-4.06 (m, 2H), 2.70-2.67 (m, 2H), 1.88-1.86 (m, 2H), 1.37-1.35 (m, 2H), 1.04-1.01 (m, 2H). MS (ESI) ink (M+H+) 217.4.

후처리

  1. customwas removed by evaporation under vacuum
  2. additionWater and Et2O were added
  3. customthe aqueous layer was separated
  4. extractionextracted with EtOAc (50 mL×3)
  5. dry with materialThe combined organic extracts dried over anhydrous Na2SO4
  6. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-d3cb88658e504163a7332c5788eb5af4
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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