Formaldehyde → 6-bromo-3,3-bis(hydroxymethyl)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one

HRID 594849

反応式

HRID 594849 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]2=[O:14].[CH2:15]=[O:16].[C:17]([O-:20])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:12])([CH3:13])[C:6]([CH2:17][OH:20])([CH2:15][OH:16])[C:5]2=[O:14]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 147553646-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

生成物 1

HCID 867242446-bromo-3,3-bis(hydroxymethyl)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one収率 86.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 6-bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (1.00 g, 3.92 mmol) and dioxane (10 mL) were added formaldehyde (37 wt. % in water, 2.95 mL, 39.2 mmol) and Na2CO3 (831 mg, 7.84 mmol) at room temperature. After stirring overnight at the same temperature, the reaction mixture was filtered. The filtrate was diluted with CHCl3, washed with 1M aqueous HCl and water, dried over MgSO4 and filtered. The filtrate was concentrated at reduced pressure, and the residue was purified with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 50%) to afford 6-bromo-3,3-bis(hydroxymethyl)-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (1.07 g).

後処理

  1. filtrationthe reaction mixture was filtered
  2. additionThe filtrate was diluted with CHCl3
  3. washwashed with 1M aqueous HCl and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated at reduced pressure
  7. customthe residue was purified with column chromatography on silica gel (hexane-EtOAc

出典と根拠

ORDレコード
ord-b10ef795afca4f99afe05562872d01ba
出典データセット
uspto-grants-2016_01
特許番号
US09242973B2

関連ノート

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