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Acetone cardice → ethyl 8-[hydroxy(phenyl)methyl]-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855062
ノート
印刷プレビュー

反応式

HRID 855062 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)=[O:2].C(=O)=O.CC(C)=O.[C:30]1([Mg]Br)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[OH:2][CH:1]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:14])[F:15])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2
参加物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 18522661Acetone cardiceHCID 86599485ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylateHCID 178418255HCID 178418255、化合物

生成物 1

HCID 69517053ethyl 8-[hydroxy(phenyl)methyl]-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 605a, Step 1 (0.45 g, 1.43 mmole) was dissolved in anhydrous THF (5 mL) and the solution was cooled to −78° C. (dry ice/acetone). Phenylmagnesium bromide (1.58 mL, 1.58 mmole) was added to the above solution dropwise, which was allowed to stir for 4 hours. The reaction was quenched with saturated ammonium chloride (20 mL) and extracted with EtOAc (2×20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give an orange oil. The oil was purified by flash chromatography (silica gel) with 100% CH2Cl2 to give a light yellow oil (0.3g, 54%): GCMS m/z 392.0 (M+). 1H NMR (CDCl3/400 MHz) 7.62 (s, 1H), 7.32 (m, 6H), 6.95 (s, 1H), 6.10 (s, 1H), 5.68 (q, 1H, J=7.0 Hz), 4.28 (m, 2H), 2.28 (s, 3H), 1.32 (m, 3H).

後処理

  1. customThe reaction was quenched with saturated ammonium chloride (20 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined extracts were washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an orange oil
  8. customThe oil was purified by flash chromatography (silica gel) with 100% CH2Cl2

出典と根拠

ORDレコード
ord-2ad4bc0f5a264434b47a153b6a480cc8
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07259266B2

反応ノート

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