p-Toluenesulfonic acid monohydrate → HCID 86706149, compound

HRID 2176302Notes

Reaction equation

HRID 2176302 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH:16]=[CH2:17])[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([O:5][C:6](=[O:7])[C:8]([CH2:13][OH:12])([CH2:9][OH:10])[CH:16]=[CH2:17])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86706150HCID 86706150, compound

Product 1

HCID 86706149HCID 86706149, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,2-dimethyl-5-vinyl-[1,3]dioxane-5-carboxylic acid tert-butyl ester (969 mg, 4 mmol) and 4-toluenesulfonic acid hydrate (76 mg, 0.4 mmol) in methanol (10 mL) was stirred at room temperature for 30 min. The solvent was evaporated and the residue was purified by silica gel chromatography using a gradient of iso-hexanes/ethyl acetate 4:1 to 1:1 to afford the title compound (660 mg, 82%) as a white solid. 1H NMR (300 MHz, d6-DMSO): δ 1.38 (s, 9H), 3.54-3.68 (m, 4H), 4.56 (t, J=5.4 Hz, 2H), 5.12 (d, J=10.5 Hz, 1H), 5.14 (d, J=18.3 Hz, 1H), 5.80 (dd, J=18.3, 10.5 Hz, 1H). LCMS (m/z) 225.2 [M+Na], Tr=1.47 min.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b869d30b96f84cc68d7d53d8fbaaac88
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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