Phenylacetic Acid → HCID 58611841, compound

HRID 2375219Notes

Reaction equation

HRID 2375219 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>ClCCl>[C:12]1([CH2:18][C:19]([O:21][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][O:22]2)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 999Phenylacetic Acid2×HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 8471Triethylamine

Product 1

HCID 58611841HCID 58611841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a saturated solution of anhydrous p-toluenesulphonic acid in dry dichloromethane (25 ml) successively phenylacetic acid (4a) (0.581 g, 4.26 mmol) and 3,4-dihydro-2H-pyran (3 ml, 32.9 mmol) were added, and the resultant solution was stirred at room temperature until the starting material 4a disappeared (ca. 1 hour). To the reaction mixture triethylamine (1 ml, 7.2 mmol) was added and the volatiles were evaporated. The obtained crude tetrahydro-2H-pyran-2-yl 2-phenylacetate (5a) was immediately utilized in the next step of the synthesis.

Workup

  1. custom(ca. 1 hour)
  2. customthe volatiles were evaporated

Sources & evidence

ORD record
ord-a91f097d8aa64a80a4446e902c3e7586
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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