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Potassium Carbonate → 2-hydroxy-6-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)benzaldehyde

HRID 1484791
ノート
印刷プレビュー

反応式

HRID 1484791 の反応式
Br[CH2:2][C:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]=1[C:9]1[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[CH:11][CH:10]=1.[OH:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[C:19]=1[CH:20]=[O:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[OH:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:2][C:3]2[CH2:8][CH2:7][O:6][CH2:5][C:4]=2[C:9]2[N:13]([CH:14]([CH3:16])[CH3:15])[N:12]=[CH:11][CH:10]=2)[C:19]=1[CH:20]=[O:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 102858012,6-DihydroxybenzaldehydeHCID 904080795-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole

生成物 1

HCID 862954162-hydroxy-6-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)benzaldehyde収率 69.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole (110 mg, 0.38 mmol) and 2,6-dihydroxybenzaldehyde (100 mg, 0.76 mmol) in DMF (6 mL) was added K2CO3 (110 mg, 0.76 mmol). After stirred at room temperature for 1 h, it was diluted with water and EtOAc, organic layer was separated, and the aqueous layer was extracted with EtOAc. Organic layer was combined, washed with brine, dried and concentrated to give crude product, which was purified by column (Hexanes/EtOAc=1:1) to give 2-hydroxy-6-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)benzaldehyde (90 mg). 1H NMR (400 MHz, CDCl3) 8 (ppm) 11.89 (s, 1H), 10.33 (s, 1H), 7.53 (d, J=1.6 Hz, 1H), 7.33 (t, J=8.8 Hz, 1H), 6.51 (d, J=8.8 Hz, 1H), 6.16 (d, J=8.0 Hz, 1H), 6.08 (d, J=2.0 Hz, 1H), 4.40 (dd, J=12.8, 6.4 Hz, 1H), 4.35 (s, 2H), 4.18 (s, 2H), 3.97 (t, J=5.2 Hz, 2H), 2.44 (s, 2H), 1.40 (d, J=6.4 Hz, 6H); MS (ESD m/z 343.3 [M+H]+.

後処理

  1. customwas separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by column (Hexanes/EtOAc=1:1)

出典と根拠

ORDレコード
ord-625d5fa57e014914ab90e5802b79a39e
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422279B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート