Lithium Hydroxide → 4-(5-Hydroxypent-1-yn-1-yl)benzoic acid

HRID 385257ノート

反応式

HRID 385257 の反応式
[Li+].[OH-].[OH:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1.CCOC(C)=O>O.C1COCC1>[OH:3][CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 11974394Methyl 4-(5-hydroxypentynyl)benzoate

生成物 1

HCID 575175834-(5-Hydroxypent-1-yn-1-yl)benzoic acid収率 93.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
42 °C

実験手順

LiOH (2 g, 83 mmol) in H2O (30 mL) was added dropwise to a stirring solution of Intermediate 20 (2 g, 9.2 mmol) in THF (30 mL). The resulting mixture was stirred at 42° C. for 4 h. After cooling, water (100 mL) and EtOAc (200 mL) were added. The mixture was extracted with EtOAc. The organic layer and the H2O layer were independently neutralized with 1N HCl. The aqueous layer was extracted with EtOAc and the combined organic layers dried over MgSO4 (s). The material was concentrated by rotary evaporation and the crude solid was purified by trituration with EtOAc and hexanes to give the title compound as a white powder (1.75 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 13.05 (brs, 1H), 7.88 (dd, 2H, J=8.5, 1.5 Hz), 7.47 (dd, 2H, J=8.5, 1.5 Hz), 4.55 (brs, 1H), 3.50 (t, 2H, J=5.5 Hz), 2.50 (m, 2H), 1.68 (m, 2H); ES/MS calcd. for C12H1O3+205.1. found m/z=205 (M+H)+.

後処理

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers dried over MgSO4 (s)
  5. concentrationThe material was concentrated by rotary evaporation
  6. customthe crude solid was purified by trituration with EtOAc and hexanes

出典と根拠

ORDレコード
ord-8d61b7b3ff3e4918a2a5475a59b5d88e
出典データセット
uspto-grants-2013_02
特許番号
US08367829B2

反応ノート

読み込み中…