3,4-dihydro-2H-pyran → HCID 57682961, compound

HRID 494312Notes

Reaction equation

HRID 494312 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:4]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 57682963HCID 57682963, compound

Product 1

HCID 57682961HCID 57682961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 g of isopropyl (1R,3S)-3-hydroxymethylcyclohexanecarboxylate and 46.2 g of dihydropyran are dissolved in 500 ml of dichloromethane and, at 0° C., 4.75 g of toluenesulfonic acid monohydrate are added. The solution is stirred overnight and then sat. sodium bicarbonate solution is added. The organic phase is separated off, diluted with MTBE and washed with sat. sodium chloride solution, dried over MgSO4 and concentrated, resulting in 140 g of isopropyl (1R,3S)-3-(tetrahydropyran-2-yloxymethyl)cyclohexanecarboxylate as brown oil.

Workup

  1. customThe organic phase is separated off
  2. additiondiluted with MTBE
  3. washwashed with sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customresulting in 140 g of isopropyl (1R,3S)-3-(tetrahydropyran-2-yloxymethyl)cyclohexanecarboxylate as brown oil

Sources & evidence

ORD record
ord-f6ad6d52afba48809105b5c7b125055b
Source dataset
uspto-grants-2009_05
Patent number
US07538131B2

Reaction notes

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