Methanol → HCID 57871421, compound

HRID 550223Notes

Reaction equation

HRID 550223 reaction equation
[OH-].[K+].C[O:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([CH2:37][CH3:38])([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH2:34][CH3:35])[CH:28]([OH:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:36])[CH:21]=3)[CH2:18][CH3:19])[CH:13]=2)[CH:8]=1)=[O:6].C1COCC1.CO>O>[CH2:18]([C:17]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:16]=[CH:15]2)([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH2:34][CH3:35])[CH:28]([OH:33])[C:29]([CH3:32])([CH3:30])[CH3:31])=[C:22]([CH3:36])[CH:21]=1)[CH2:37][CH3:38])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 57871401HCID 57871401, compound

Product 1

HCID 57871421HCID 57871421, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Add KOH (321 mg, 5.724 mmol) to a mixture of diastereomeric isomer pair 1 of 6-{1-ethyl-1-[4-(1-ethyl-2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]propyl}-naphthalene-2-carboxylic acid methyl ester (702 mg, 1.431 mmol), THF (9 ml), MeOH (3 ml), and H2O (1 ml). Heat the reaction mixture to 60° C. and stir it for 14 h. Cool and partition the reaction mixture between Et2O and 1N HCl. Dry the organic layer over MgSO4, filter, and concentrate the filter in vacuo to give the title compound as a glassy solid (665 mg, 97%). 1NMR (400 MHz, CDCl3) δ ppm: 0.64 (t, J=7.6 Hz, 6H), 0.93 (t, J=8.4 Hz, 3H), 0.93 (s, 9H), 1.72 (m, 1H), 1.82 (m, 1H), 2.12 (s, 3H), 2.19 (q, 4H), 3.28 (s, 1H), 4.28 (dd, J=6.0, 3.2 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 6.90 (d, J=2.0 Hz, 1H), 6.94 (dd, J=6.0, 2.4 Hz, 1H), 7.21 (dd, J=7.2, 1.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.86 (s, 1H), 7.89 (d, J=8.8 Hz, 1H), 8.09 (dd, J=6.8, 1.6 Hz, 1H), 8.62 (s, 1H). High Res. ES-MS: 499.2832; calc. for C31H40O4+Na: 499.2825.

Workup

  1. temperatureCool
  2. custompartition the reaction mixture between Et2O and 1N HCl
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate the
  6. filtrationfilter in vacuo

Sources & evidence

ORD record
ord-a466fca57b0b44e188f8e8f1ca762a33
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

Loading…