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

HRID 385257노트

반응식

HRID 385257 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
42 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-8d61b7b3ff3e4918a2a5475a59b5d88e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367829B2

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