Methanol → HCID 57223296, compound

HRID 1934546Notes

Reaction equation

HRID 1934546 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].C[O-].[Na+].CO.[CH:17]1([CH:23]=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(OC)(OC)OC>[CH:17]1([CH:23]=[CH:1][C:2]([C:4]2[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=2[OH:11])=[O:3])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 887MethanolHCID 16275CyclohexanecarboxaldehydeHCID 959922-Acetyl-4-fluorophenolHCID 10942334Sodium Methoxide

Product 1

HCID 57223296HCID 57223296, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

A mixture of 5-fluoro-2-hydroxyacetophenone on Wang resin (4.0 g, 4.6 mmol) was swelled in trimethyl orthoformate (40 mL) for 10 min. 25% NaOMe in MeOH (2.0 g, 9.2 mmol) was added and the mixture was stirred for 45 min. Cyclohexanecarboxaldehyde (1.5 g, 13.8 mmol) was added and stirring was continued for 40 min. The resin was filtered and washed with alternating MeOH and CH2Cl2 (×5) and dried under high vacuum overnight to give 4.3 g of 3-cyclohexyl-1-(2-hydroxy-5-fluorophenyl)-2-propen-1-one on Wang resin.

Workup

  1. stirringstirring
  2. waitwas continued for 40 min
  3. filtrationThe resin was filtered
  4. washwashed with alternating MeOH and CH2Cl2 (×5)
  5. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-74fd29908dab473a980734395aa5d81e
Source dataset
uspto-grants-2002_05
Patent number
US06384060B1

Reaction notes

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