Potassium Hydroxide → HCID 86001751, compound

HRID 873263Notes

Reaction equation

HRID 873263 reaction equation
[OH-].[K+].[O:3]=[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([C:32]([O:34]CC)=[O:33])([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:26])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([C:16]([O:18]CC)=[O:17])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10]>CCO>[CH2:14]([O:13][C:11]([C:9]([CH3:10])([CH2:8][CH2:7][CH2:6][CH2:5][C:4](=[O:3])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:26])[C:32]([OH:34])=[O:33])[C:16]([OH:18])=[O:17])=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 86001739HCID 86001739, compound

Product 1

HCID 86001751HCID 86001751, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of KOH (2.44 g, >85%, >37.0 mmol) in EtOH (80 mL) was added to 106h (9.00 g, 18.5 mmol). After stirring for 54 h, another portion of KOH (1.21 g, >85%, >18.5 mmol) was added and stirring was continued for 16 h. The reaction mixture was evaporated in vacuo and Et2O (250 mL) and H2O (250 mL) were added. The aqueous layer was separated, acidified with aqueous HCl (2 M, 50 mL) and extracted with Et2O (250 mL) and CH2Cl2 (250 mL). The combined organic layers were dried and the remaining residue was purified by column chromatography (silica, heptane:EtOAc:HOAc=3:2:0.01) and vacuum dried at 50° C. to give 107h (6.43 g, 81%) as a yellow oil. 1H NMR: δ 10.40 (br s, 2H), 4.21 (q, J=7.1 Hz, 4H), 2.42 (t, J=7.4 Hz, 4H), 1.90-1.84 (m, 4H), 1.59 (quintet, J=7.4 Hz, 4H), 1.43 (s, 6H), 1.32-1.19 (m, 4H), 1.27 (t, J=7.2 Hz, 6H). 13C NMR: δ 210.9, 177.7 (2×), 172.1 (2×), 61.5 (2×), 53.5 (2×), 42.2 (2×), 35.3 (2×), 23.8 (2×), 23.7 (2×), 19.8 (2×), 13.9 (2×). HRMS calcd for C21H35O9 (MH+): 431.2281, found: 431.2298.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h
  3. customThe reaction mixture was evaporated in vacuo and Et2O (250 mL) and H2O (250 mL)
  4. additionwere added
  5. customThe aqueous layer was separated
  6. extractionextracted with Et2O (250 mL) and CH2Cl2 (250 mL)
  7. customThe combined organic layers were dried
  8. customthe remaining residue was purified by column chromatography (silica, heptane:EtOAc:HOAc=3:2:0.01) and vacuum
  9. customdried at 50° C.

Sources & evidence

ORD record
ord-316ca4b50ba348abadf34df37f822c4b
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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