Water → HCID 131722851, compound

HRID 1596140Notes

Reaction equation

HRID 1596140 reaction equation
[CH3:1][C@H:2]1[C@:6]23[CH2:11][C@H:10]([C:12]([CH3:14])([CH3:13])[C@@H:5]2[CH2:4][CH2:3]1)[C@@:9]([OH:16])([CH3:15])[CH2:8][CH2:7]3.C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26].[OH2:29]>O1CCCC1.C(OCC)(=O)C>[CH3:1][C@H:2]1[C@:6]23[CH2:11][C@H:10]([C:12]([CH3:14])([CH3:13])[C@@H:5]2[CH2:4][CH2:3]1)[C@@:9]([OH:16])([CH3:15])[CH2:8][CH2:7]3.[C:24]([O-:27])(=[O:29])[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 65575(+)-Cedrol

Product 1

HCID 131722851HCID 131722851, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 200 ml of tetrahydrofuran, 25 g of (+)-Cedrol (manufactured by Lancaster) was dissolved, and to the solution were added 22.8 g of triethylamine and 1 g of N,N-dimethylaminopyridine. To the solution was dropwise added 15.2 g of acrylic chloride under cooling with ice over a period of 30 minutes and the mixture was stirred at room temperature for 2 days. To the reaction solution was added 100 ml of distilled water under cooling with ice, and the mixture was stirred for 30 minutes and 300 ml of ethyl acetate was added thereto. The water layer was removed by separation and the organic layer was washed with water, dried and concentrated to obtain a crude product. The crude product was purified by column chromatography to obtain 18.2 g of the desired compound which is a raw material monomer for repeating unit (b5).

Workup

  1. temperatureunder cooling with ice over a period of 30 minutes
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 30 minutes
  4. customThe water layer was removed by separation
  5. washthe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customto obtain a crude product
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-3099e4635a7b434e96775e5cfbbad195
Source dataset
uspto-grants-2001_09
Patent number
US06291130B1

Reaction notes

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