Hydroxyamine hydrochloride → ((R)-1-benzyloxymethyl-3-butenyloxy)acetaldehyde oxime

HRID 68390

반응식

HRID 68390 반응식
C(O[CH:4](OCC)[CH2:5][O:6][C@H:7]([CH2:17][CH:18]=[CH2:19])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.Cl.[NH2:24][OH:25]>C(O)(=O)C.O.COC(C)(C)C>[CH2:10]([O:9][CH2:8][C@H:7]([O:6][CH2:5][CH:4]=[N:24][OH:25])[CH2:17][CH:18]=[CH2:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 2

HCID 443297Hydroxyamine hydrochloride2회HCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

생성물 1

HCID 86640913((R)-1-benzyloxymethyl-3-butenyloxy)acetaldehyde oxime

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 15413tert-Butyl methyl ether용매

실험 절차

({[(2R)-2-(2,2-Diethoxyethoxy)pent-4-en-1-yl]oxy}methyl)benzene (C2) (12.4 g, 40.2 mmol) was dissolved in acetic acid (28 mL) and water (12 mL). Hydroxylamine hydrochloride (2.84 g, 40.9 mmol) was added as a solid. After 1 hour, additional hydroxylamine hydrochloride (2.84 g, 40.9 mmol) was added. After 1 more hour, the reaction mixture was diluted with tert-butyl methyl ether (100 mL) and washed with water (3×50 mL), then washed with aqueous potassium carbonate solution (0.5 M, 100 mL). The organic layer was concentrated to provide the product as a pale yellow oil, which consisted of a roughly equimolar mixture of oxime isomers, as assessed by 1H NMR. Yield: 9.60 g, 38.5 mmol, 96%. 1H NMR (400 MHz, CDCl3) δ 7.98 and 7.67 (2 br s, total 1H), [7.50 (t, J=5.6 Hz) and 6.95 (t, J=3.6 Hz), total 1H], 7.28-7.39 (m, 5H), 5.74-5.87 (m, 1H), 5.04-5.14 (m, 2H), 4.55 and 4.56 (2 s, total 2H), 4.47-4.49 (m, 1H), 4.18-4.28 (m, 1H), 3.47-3.65 (m, 3H), 2.30-2.37 (m, 2H).

후처리

  1. washwashed with water (3×50 mL)
  2. washwashed with aqueous potassium carbonate solution (0.5 M, 100 mL)
  3. concentrationThe organic layer was concentrated

출처 및 근거

ORD 기록
ord-f31db13c1a4b4e418e77c1b0f046ff2b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822456B2

연결된 노트

불러오는 중…