Ethanol → HCID 18988249, compound

HRID 2396116Notes

Reaction equation

HRID 2396116 reaction equation
[CH2:1]([CH:6]1[CH:11]=[CH:10][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[S:8][CH:7]1[C:17]([O:19]CC)=[O:18])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].C(O)C>>[CH2:1]([CH:6]1[CH:11]=[CH:10][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[S:8][CH:7]1[C:17]([OH:19])=[O:18])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18988220HCID 18988220, compound

Product 1

HCID 18988249HCID 18988249, compound

Procedure

Part C. A solution of the ester compound from Part B above (4.53 g, 14.5 mmol) and sodium hydroxide (0.25N solution) in 95% ethanol (120 mL, 30.0 mmol NaOH) was stirred for 12 hours at ambient temperature. The reaction mixture was evaporated, and the residue acidified with hydrochloric acid (1N, 150 mL). This was saturated with sodium chloride and extracted with methylene chloride (2×200 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the product, 3,6-dipentyl-3,6-dihydro-2H-thiopyran-2-carboxylic acid, as an oily mixture of diastereomeric products (5:1 by NMR) (4.01 g, 14.1 mmol, 97%). 1H NMR (major isomer; CDCl3): δ 5.73 (2H, s); 3.48 (1H, br t, J=7 Hz); 3.40 (1H, d, J=3.7 Hz); 2.60-2.52 (1H, m); 1.71-1.24 (16H, m); 0.89 (6H, t, J=3.7 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 287 (6%); 286 (18%); 285 (100%); 239 (25%); 211 (2%).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionThis was saturated with sodium chloride and extracted with methylene chloride (2×200 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cd2a147c4c654d19bf8c5735bcd494b5
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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