(R)Methyl 1-(((1-(3-(hydroxymethyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)methyl)cyclopropaneacetate → Methyl 1-(((1 (R)-(3-formylphenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetate

HRID 2226985Notes

Reaction equation

HRID 2226985 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C@H:9]([S:22][CH2:23][C:24]2([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:26][CH2:25]2)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([OH:21])([CH3:20])[CH3:19])[CH:6]=[CH:7][CH:8]=1>CCOC(C)=O.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[C:5]([C@H:9]([S:22][CH2:23][C:24]2([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:25][CH2:26]2)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([OH:21])([CH3:20])[CH3:19])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 18655248(R)Methyl 1-(((1-(3-(hydroxymethyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)methyl)cyclopropaneacetate

Product 1

HCID 22857739Methyl 1-(((1 (R)-(3-formylphenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst3×HCID 8857Ethyl AcetateSolvent

Procedure

To the dihydroxy ester from Step 15 (6.8 g, 15.4 mmol) in EtOAc (150 mL) at 50° C. was added MnO2 (6.7 g, 76.8 mmol). After stirring for 30 minutes at 50° C. more MnO2 (6.7 g) was added, and 30 minutes later, a third portion of MnO2 (6.7 g) was added. An hour later, the warm reaction mixture was filtered through celite and the cake was washed with additional EtOAc. Evaporation of the solvents gave the title aidehyde 5.62 g (83%). 1H NMR (CD3COCD3): δ5 10.4 (1H, s), 7.9 (1H, br s), 7.8 (2H, m), 7.58 (1H, t), 7.38 (1H, br d), 7.1 (3H, m), 4.1 (1H, t), 3.54 (3H, s), 3.13 (1H, ddd), 2.85 (1H, ddd), 2.51 (2H, s), 2.49 (2H, d), 2.2 (2H, m), 1.51 (6H, s), 0.52-0.32 (4H, m).

Workup

  1. additionwas added
  2. customAn hour later, the warm reaction mixture
  3. filtrationwas filtered through celite
  4. washthe cake was washed with additional EtOAc
  5. customEvaporation of the solvents
  6. customgave the title aidehyde 5.62 g (83%)

Sources & evidence

ORD record
ord-66974f4d285c4dc88cfc292f7f171e54
Source dataset
uspto-grants-1994_09
Patent number
US05350760

Reaction notes

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