p-Toluenesulfonic acid → HCID 58611847, compound

HRID 2375209Notes

Reaction equation

HRID 2375209 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1)=[O:15].[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.C(N(CC)CC)C>ClCCl>[O:24]=[C:23]([O:25][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][O:26]1)[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 107978792-(4-(Methoxycarbonyl)phenyl)acetic acid

Product 1

HCID 58611847HCID 58611847, compoundYield 170.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a saturated solution of anhydrous p-toluenesulphonic acid in dry dichloromethane (35 ml) successively 2-[4-(methoxycarbonyl)phenyl]acetic acid (E11) (0.671 g, 3.45 mmol) and 3,4-dihydro-2H-pyran (3 ml, 32.9 mmol) were added, and the resultant solution was stirred for 45 minutes at room temperature. To the reaction mixture triethylamine (1 ml, 7.2 mmol) was added and the volatiles were evaporated. The obtained crude title product (1.64 g) was immediately utilized in the next step of the synthesis.

Workup

  1. customthe volatiles were evaporated

Sources & evidence

ORD record
ord-b11a2da32040422cb461cde9f5bcb543
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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