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

HRID 2103039
ノート
印刷プレビュー

反応式

HRID 2103039 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒
2 回

反応条件

温度
0 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-50b2db4e5fca4dc6ae65d2f1da1cfae1
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576094B2

反応ノート

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