Hydrochloric Acid → HCID 49765928, compound

HRID 1420695Notes

Reaction equation

HRID 1420695 reaction equation
[C:1]1([CH2:7][C@H:8]([OH:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1>[C:1]1([CH2:7][C@H:8]([O:10][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 53246311-Phenyl-2-propanol, (-)-

Product 1

HCID 49765928HCID 49765928, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

(2R)-1-Phenyl-2-propanol (0.5 ml, 3.65 mmol) was added dropwise to a solution of p-toluenesulfonyl chloride (0.73 g, 3.83 mmol) in pyridine) (3 ml) at 0° C. The mixture was stirred at 0° C. under nitrogen for 30 minutes then at room temperature overnight. The reaction mixture was poured into 2M hydrochloric acid (75 ml) and extracted with diethyl ether (2×50 ml). The extracts were washed with 2M hydrochloric acid (50 ml), saturated sodium hydrogen carbonate (50 ml) and brine (50 ml), combined, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (0.95 g, 90%); δH (250MHz, CDCl3) 1.30 (3H, d, J 6.2Hz, CHCH3), 2.42 (3H, s, ArCH3), 2.77 (1H, dd, J 13.8, 6.6Hz, CH(OTs)CHAHBPh), 2.92 (1H, dd, J 13.8, 6.6Hz, CH(OTs)CHAHBPh), 4.74 (1H, m, CHOTs), 7.03 (2H, m, ArH), 7.20 (5H, m, ArH), 7.62 (1H, m. ArH).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionextracted with diethyl ether (2×50 ml)
  4. washThe extracts were washed with 2M hydrochloric acid (50 ml), saturated sodium hydrogen carbonate (50 ml) and brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9b1eb6ffaf249d2a76a3ef5f70f6610
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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