Water → HCID 57124206, compound

HRID 1906215Notes

Reaction equation

HRID 1906215 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].N1CCC[CH2:16]1.[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22]C=1.O.[CH2:28]([O:30][C:31](=[O:33])[CH3:32])[CH3:29].C1(C)C=CC=CC=1>>[O:30]1[CH2:28][CH2:29][CH2:16][CH2:32][CH:31]1[O:33][CH2:22][CH2:23][CH2:24][CH2:25][C:20]1([CH3:26])[CH2:13][C:11](=[O:12])[C:8]2[CH:7]=[CH:6][C:5]([OH:14])=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=2[O:10]1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 31268PyrrolidineHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 21584019Toluene ethylacetate

Product 1

HCID 57124206HCID 57124206, compound

Procedure

A mixture of 2.54 g of 6-hydroxy-2-hexanone tetrahydropyranyl ether, 2.46 g of 2,4-dihydroxy-3-propylacetophenone, 1.05 g of pyrrolidine, and 35 ml of toluene was stirred at room temperature for four days. The dark brown solution was then refluxed for 24 hours, with water removal using a Dean-Stark trap. A mixture of 1:1 ethylacetate-toluene (400 ml) and 50 g of silica were added to the reaction mixture and the slurry was stirred for 1 hour at room temperature. The silica gel was filtered with suction and washed with 1:1 ethyl acetate-toluene. The filtrate and washes were combined and concentrated in vacuo. The residual oil was purified by column chromatography on silica gel. Hexane-ethyl acetate (2:1) eluted 3.3 g (69.1%) of rac.-2,3-dihydro-2-[4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl]-2-methyl-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, as a dark brown oil.

Workup

  1. additionwere added to the reaction mixture
  2. stirringthe slurry was stirred for 1 hour at room temperature
  3. filtrationThe silica gel was filtered with suction
  4. washwashed with 1:1 ethyl acetate-toluene
  5. concentrationconcentrated in vacuo
  6. customThe residual oil was purified by column chromatography on silica gel
  7. washHexane-ethyl acetate (2:1) eluted 3.3 g (69.1%) of rac.-2,3-dihydro-2-[4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl]-2-methyl-7-hydroxy-8-propyl-4H-1-benzopyran-4-one

Sources & evidence

ORD record
ord-6bc619f74df44528992b10995f04e1e8
Source dataset
uspto-grants-1987_03
Patent number
US04650812

Reaction notes

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