Ethanol → HCID 69512330, compound

HRID 970257Notes

Reaction equation

HRID 970257 reaction equation
O1CCCCC1[O:7][C:8]1[CH:33]=[CH:32][C:11]([CH:12]=[CH:13][C:14]([O:16][C@@H:17]2[CH:21]3[O:22][CH2:23][C@@H:24]([O:25]C4CCCCO4)[CH:20]3[O:19][CH2:18]2)=[O:15])=[CH:10][CH:9]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(O)C>O>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[CH:13][C:14]([O:16][C@@H:17]2[CH:21]3[O:22][CH2:23][C@@H:24]([OH:25])[CH:20]3[O:19][CH2:18]2)=[O:15])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 69511759HCID 69511759, compound

Product 1

HCID 69512330HCID 69512330, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 9.1 g of 3-(R)-(tetrahydropyran-2-yloxy)-hexahydro-furo[3,2-b]furan-6-(S)-yl 4-(tetrahydropyran-2-yloxy)cinnamate (25), 0.48 g of pyridinium 4-toluenesulfonate and 60 ml of absolute ethanol was heated at 60° C. for 3 hours under a nitrogen atmosphere. A clear solution was obtained which was added dropwise to 50 g of ice and 100 g of water with vigorous stirring. A white solid precipitated. It was filtered off, washed with water and dried in a dessicator over silica. 3.7 g of a white powder was obtained (yield: 66%).

Workup

  1. customA clear solution was obtained which
  2. customA white solid precipitated
  3. filtrationIt was filtered off
  4. washwashed with water
  5. customdried in a dessicator over silica

Sources & evidence

ORD record
ord-515ef93cb5d74b3eae5f870180c9f7ed
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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