3,4-dihydro-2H-pyran → HCID 69601101, compound

HRID 2215082Notes

Reaction equation

HRID 2215082 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][S:6][C:5](=[O:8])[NH:4]1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:1][CH2:2][C@H:3]1[CH2:7][S:6][C:5](=[O:8])[NH:4]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 55288328HCID 55288328, compound

Product 1

HCID 69601101HCID 69601101, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-3 (3.3 g, 25 mmol) and 20 mg of p-toluenesulfonic acid in CH2Cl2 (100 mL) was added 3,4-dihydro-2H-pyran (2.7 mL, 30 mmol) and the resulting solution was stirred at rt for 30 minutes. Triethylamine (0.1 mL) was added and the solution was concentrated in vacuo. The compound was purified by flash chromatography using 40% EtOAc/hexanes to yield 4 g of 3-4 as a colorless oil. 1H NMR (400 MHz, acetone-d6): δ 7.0 (br s, 1H), 4.6 (s, 1H), 4.0 (m, 1H), 3.8 (m, 2H), 3.6 (m, 3H), 3.3 (dd, 1H), 1.9–1.4 (m, 6H).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-cf79a5f571614b9f85bd3f7aed34a75c
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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