Dichloromethane → HCID 131716472, compound

HRID 2166002

Reaction equation

HRID 2166002 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])C(Cl)=O.[OH:24][C:25]1[CH:30]=[CH:29][C:28](C2C=CC(C(OC[C@@H](C)CC)=O)=CC=2)=[CH:27][CH:26]=1.C(Cl)Cl.[C:48](OCC)(=[O:50])C>N1C=CC=CC=1>[F:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:9]([CH:8]=[CH:4][CH:3]=1)[C:48]([O:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:50]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 139075384'-[(S)-2-methylbutoxycarbonyl]biphenyl-4-olHCID 150952233-Fluoro-4-dodecyloxybenzoic acid chloride

Product 1

HCID 131716472HCID 131716472, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Fluoro-4-dodecyloxybenzoic acid chloride (3.32 g: 10 mmols) and 2.84 g (10 mmols) of (S)-2-methylbutyl 4'-hydroxybiphenyl-4-carboxylate were reacted in 10 ml of pyridine and 15 ml of methylene chloride for 3 hours under reflux. After the reaction mixture was left to cool, 50 ml of ethyl acetate was added, and washed twice with 10% hydrochloric acid and once with each of a saturated sodium bicarbonate aqueous solution, water and a saturated sodium chloride aqueous solution. After the reaction product was dried with anhydrous sodium sulfate, the solvent was concentrated. Crude crystals obtained were purified by silica gel column chromatography (solvent: chloroform-hexane), and recrystallized from ethanol to obtain 4.64 g of 4{(S)-2-methylbutyloxycarbonyl]phenyl)phenyl 3-fluoro-dodecyloxybenzoate.

Workup

  1. waitAfter the reaction mixture was left
  2. temperatureto cool
  3. washwashed twice with 10% hydrochloric acid
  4. dry with materialAfter the reaction product was dried with anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated
  6. customCrude crystals obtained
  7. customwere purified by silica gel column chromatography (solvent: chloroform-hexane)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8fd63501fdbe4a128189ddda3b992b1f
Source dataset
uspto-grants-1990_07
Patent number
US04943386

Linked notes

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