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

HRID 468297ノート

反応式

HRID 468297 の反応式
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

参加物

5

反応物 3

HCID 887Methanol2 回HCID 168937Lithium hydroxide, monohydrateHCID 59129159methyl 1-(3,4-dihydro-2H-chromen-6-yl)cyclopropane-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d3cb88658e504163a7332c5788eb5af4
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

読み込み中…