Hydrochloric Acid → 2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-ol

HRID 1427839

반응식

HRID 1427839 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.Cl>CO.[Zn]>[CH3:12][C:8]1([CH3:13])[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)[O:9]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

생성물 1

HCID 110412812,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-ol수율 62.6%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

A mixture of 7-hydroxy-2,2-dimethylchroman-4-one (500 mg, 2.60 mmol) and HCl (conc. 10 mL) in MeOH (30 mL) was stirred at 0° C. for 10 min, then zinc power (300 mg) was added slowly. After stirring at room temperature for 16 hrs, the solvents were removed under reduced pressure and the mixture was extracted with EtOAc (150×3 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by reverse phase column flash (28%-35% MeCN in 0.5% NH4HCO3) to give target product of 2,2-dimethylchroman-7-ol (290 mg, 62%) as a brown yellow solid. LCMS (ESI) m/z: 177.1 [M−H]+; 1H-NMR (500 MHz, CDCl3): δ 6.89 (d, J=8.0 Hz, 1H), 6.34 (dd, J=8.5, 2.5 Hz, 1H), 6.27 (d, J=2.5 Hz, 1H), 4.70 (s, 1H), 2.69 (t, J=13.5, 7.0 Hz, 2H), 1.77 (t, J=13.5, 7.0 Hz, 2H), 1.32 (s, 6H).

후처리

  1. stirringAfter stirring at room temperature for 16 hrs
  2. customthe solvents were removed under reduced pressure
  3. extractionthe mixture was extracted with EtOAc (150×3 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse phase column flash (28%-35% MeCN in 0.5% NH4HCO3)

출처 및 근거

ORD 기록
ord-d9fc11a0594140398409073dc59cbdca
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933236B2

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