(-)DIP-Chloride → HCID 57757247, compound

HRID 227897

Reaction equation

HRID 227897 reaction equation
B(Cl)([C@H]1[C@H](C)C2C(C)(C)C(CC2)C1)[C@H]1[C@H](C)C2C(C)(C)C(CC2)C1.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:33]1[CH:38]=[CH:37][C:36]([C:39](=[O:45])[CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44])=[CH:35][CH:34]=1>CCOCC>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:33]1[CH:38]=[CH:37][C:36]([C@@H:39]([OH:45])[CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 16212015(-)DIP-ChlorideHCID 577572631-(2',4'-Dichloro-biphenyl-4-yl)-hex-5-en-1-one

Product 1

HCID 57757247HCID 57757247, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(−)DIP-Chloride (2.4 g) was dissolved in dry ether (10 mL) and cooled in an ethanol/CO2 bath. 1-(2′,4′-Dichloro-biphenyl-4-yl)hex-5-en-1-one (1 g) was dissolved in dry ether (5 mL) and added dropwise to the DIP solution. The mixture was allowed to warm to room temperature and stirred for 24 hours. Petrol (50 mL) was added and the organic layer separated. The aqueous was diluted with water and extracted with a further 50 mL petrol. The organics were combined, dried and evaporated to give a thick oil. It was not possible to obtain a pure sample by column chromatography, but no trace of starting material remained, as assessed by thin layer chromatography.

Workup

  1. temperaturecooled in an ethanol/CO2 bath
  2. additionadded dropwise to the DIP solution
  3. customthe organic layer separated
  4. additionThe aqueous was diluted with water
  5. extractionextracted with a further 50 mL petrol
  6. customdried
  7. customevaporated
  8. customto give a thick oil
  9. customto obtain a pure sample by column chromatography

Sources & evidence

ORD record
ord-3e9d5568650a434c932db9970c182564
Source dataset
uspto-grants-2009_07
Patent number
US07560597B2

Linked notes

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