Methanol → HCID 57223296, compound

HRID 1934530Notes

Reaction equation

HRID 1934530 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-364ee5a37b9f4fb3abb924b32b427fa0
Source dataset
uspto-grants-2002_05
Patent number
US06384058B1

Reaction notes

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