홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium Methoxide → 7,8-Dimethyl-5[(Z)-2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1'-cyclobutan]-6-ol

HRID 2103039
노트
인쇄 미리보기

반응식

HRID 2103039 반응식
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)C=CC=CC=1.C[O-].[Na+].[OH:35][C:36]1[C:48]([CH3:49])=[C:47]([CH3:50])[C:46]2[O:45][C:41]3([CH2:44][CH2:43][CH2:42]3)[CH2:40][CH2:39][C:38]=2[C:37]=1[CH:51]=O>C1COCC1>[CH3:49][C:48]1[C:47]([CH3:50])=[C:46]2[C:38]([CH2:39][CH2:40][C:41]3([O:45]2)[CH2:42][CH2:43][CH2:44]3)=[C:37](/[CH:51]=[CH:9]\[C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[C:36]=1[OH:35]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 23163315Triphenyl[(quinolin-2-yl)methyl]phosphanium bromideHCID 866054866-Hydroxy-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-5-carbaldehyde

생성물 1

HCID 1363641377,8-Dimethyl-5[(Z)-2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1'-cyclobutan]-6-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
2회

반응 조건

온도
0 °C

실험 절차

MS (m/z)=404 (M+H+). To a suspension of 0.35 g of triphenyl(quinolin-2-ylmethyl)phosphonium bromide in 5 mL of THF was added 3 mL of 0.5 M sodium methoxide at 0° C under Argon, followed by a solution of 6-Hydroxy-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-5-carbaldehyde 0.18 g) in 10 mL of THF. The solution was stirred for 1 hr at 0° C., warmed to room temperature, and stirred for 2 hrs. The tetrahydrofuran was evaporated, and the residue was partitioned between EtOAc and H2O, washed with brine, then dried over Na2SO4. The crude material was purified on a silica column eluting with 1:8 EtOAc/Hexane. 50 mg of 7,8-dimethyl-5-[2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1′-cyclobutan]-6-ol which was precipitated with hexane. 1H-NMR (300 MHz, CDCl3) δ=1.70-1-76 (m, 3H), 1.78-1.97 (m, 5H), 2.09-2.30 (m, 8H), 2.81-2.85 (t, 2H), 5.70 (brs, 1H), 7.18-7.24 (d, 1H), 7.50-7.56 (m, 2H), 7.71-7.82 (m, 3H), 8.08-8.13 (m, 2H) ppm. 13C-NMR (75 MHz, CDCl3) δ=12.24, 12.34, 12.60, 21.25, 29.31, 34.10, 76.51, 117.47, 119.17, 119.65, 112.33, 126.29, 126.46, 127.45, 127.55, 129.23, 129.88, 130.01, 133.47, 136.49, 145.10, 155.55 ppm. MS (m/z)=372 (M+H+).

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred for 2 hrs
  3. customThe tetrahydrofuran was evaporated
  4. customthe residue was partitioned between EtOAc and H2O
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe crude material was purified on a silica column
  8. washeluting with 1:8 EtOAc/Hexane
  9. custom50 mg of 7,8-dimethyl-5-[2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1′-cyclobutan]-6-ol which was precipitated with hexane

출처 및 근거

ORD 기록
ord-50b2db4e5fca4dc6ae65d2f1da1cfae1
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576094B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트