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

HRID 873703

반응식

HRID 873703 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f6a898fcf4443d6a650731eb9a3951e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975415B2

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