3,4-dihydro-2H-pyran → HCID 12042330, compound

HRID 1420130Notes

Reaction equation

HRID 1420130 reaction equation
[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][C:7](=[O:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([OH:26])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1.[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.[C:33]([O-:36])(O)=O.[Na+]>C(Cl)Cl>[O:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]1[O:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][C:7](=[O:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([O:26][CH:4]1[CH2:3][CH2:2][CH2:10][CH2:33][O:36]1)[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 12042329HCID 12042329, compound

Product 1

HCID 12042330HCID 12042330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.2 g (3.2 mmol) of diol 26 and 0.05 g of ptoluenesulfonic acid monohydrate in 100 mL of CH2Cl2 at 0° C. was treated with 3,4-dihydro-2H-pyran (1.1 ml, 12 mmol) and the solution was stirred for 2 h at 0° C. After pouring into saturated NaHCO3, phases were separated and the organic layer was dried over MgSO4, filtered, concentrated, and purified by chromatography on silica gel (1/1, hexanes/EtOAc) to afford 1.1 g of 27 as a clear, colorless oil. 1H NMR (CDCl3) δ 8.04 (dd, J=7.0, 1.6, 1 H), 7.44 (m, 2 H), 7.12 (m, 1 H), 4.95 (dt, 1 H), 4.8 (m, 1 H), 4.7 (m, 2 H), 4.15-3.80 (m, 4 H), 3.5 (m, 2 H), 2.82 (dd, J=10.8,1 H), 2.55 (m, 2 H), 2.3 (m, 1 H), 2.1-1.3 (m, 6 H).

Workup

  1. customwere separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel (1/1, hexanes/EtOAc)

Sources & evidence

ORD record
ord-76aafb52cc4f4310b201e880bdc397bd
Source dataset
uspto-grants-1999_03
Patent number
US05889052

Reaction notes

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