3,4-dihydro-2H-pyran → HCID 66978150, compound

HRID 1666744Notes

Reaction equation

HRID 1666744 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][CH2:16][C:17]([OH:19])=O)([CH3:14])[CH2:6][CH2:5]2.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>ClCCl.C1COCC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH3:14][C:7]1([CH2:15][CH2:16][CH2:17][OH:19])[CH2:6][CH2:5][C:4]2[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([O:1][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][O:20]3)[CH:3]=2)[O:8]1

Participants

7

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 1330982,7,8-Trimethyl-2-(beta-carboxy-ethyl)-6-hydroxychromanHCID 21226445Aluminium lithium hydride

Product 1

HCID 66978150HCID 66978150, compound

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(6-hydroxy-2,7,8-trimethyl-chroman-2-yl)-propionic acid (500 mg), 3,4-dihydro-2-H-pyran (2 mL) and pyridinium p-toluenesulfonate (PPTS) (50 mg) in dichloromethane (20 mL) was stirred at RT for overnight. The mixture was washed with water, dried over MgSO4, and concentrated to give an oily residue. The oil was dissolved in THF, then LiAlH4 (85 mg) was added and the mixture was stirred at RT for 2 h. The excess LiAlH4 was destroyed by adding ethyl acetate, and the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography eluting with 30% EtOAc in hexane to give 732 mg of 3-[2,7,8-trimethyl-6-(tetrahydro-pyran-2-yloxy)-chroman-2-yl]-propan-1-ol as an oily product. 1H-NMR (300 MHz, CDCl3) δ (ppm): 6.67 (s, 1H), 5.32 (t, J=3.2 MHz, 1H), 4.0-3.9 (m, 1H), 3.70-3.55 (m, 3H), 2.75-2.70 (m, 2H), 2.15, 2.09 (2s, 6H), 2.10-1.60 (m, 12H), 1.25 (s, 3H). 13C-NMR (75 MHz, CDCl3) δ (ppm): 148.08, 146.23, 125.51, 125.25, 117.66, 112.99, 112.96, 97.36, 75.17, 63.25, 62.09, 60.41, 36.26, 36.03, 31.51, 31.47, 30.78, 26.97, 25.41, 24.01, 23.81, 22, 48, 21.05, 19.11, 14.19, 12.18, 11.94.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give an oily residue
  5. stirringthe mixture was stirred at RT for 2 h
  6. customThe excess LiAlH4 was destroyed
  7. additionby adding ethyl acetate
  8. additionthe mixture was poured into water
  9. extractionextracted with EtOAc
  10. washThe organic layer was washed with water
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel column chromatography
  14. washeluting with 30% EtOAc in hexane

Sources & evidence

ORD record
ord-9da7adfecbf5423681ded0111b1ee2b5
Source dataset
uspto-grants-2011_10
Patent number
US08044097B2

Reaction notes

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