Hydrochloric Acid → HCID 21932013, compound

HRID 750772Notes

Reaction equation

HRID 750772 reaction equation
[C:1]([C:4]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=[O:20])[CH2:6][CH2:5]1)([OH:3])=[O:2].[OH-].[Na+].[BH4-].[Na+].Cl>CC(O)C.O>[C:1]([C:4]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([OH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([CH3:22])([CH3:23])[C:19]([OH:21])=[O:20])[CH2:5][CH2:6]1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 11674524HCID 11674524, compound

Product 1

HCID 21932013HCID 21932013, compoundYield 107.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a mixture of 13-(1-carboxycyclopropyl)-2,2-dimethyl-8-oxotridecanoic acid (3.67 g, 10.8 mmol) in iPrOH (20 mL) and H2O (20 mL) was added NaOH (0.90 g, 22.5 mmol). After 5 min of stirring, NaBH4 (0.20 g, 5.3 mmol) was added to the resulting clear solution. Additional NaBH4 (0.10 g) was added after 100 min of stirring. After 16 h, the mixture was acidified to pH˜1 with aqueous HCl (1M) and extracted with Et2O (3×50 mL). The combined organic phases were washed with brine (2×50 mL), dried (Na2SO4), evaporated in vacuo and coevaporated in vacuo from EtOAc (2×15 mL) to give 13-(1-carboxycyclopropyl)-8-hydroxy-2,2-dimethyltridecanoic acid (3.99 g, 97%, contains 10% (w/w) EtOAc) as a viscous colorless oil. 1H NMR (CD3OD): δ=3.48 (m, 1H), 1.50-1.21 (m, 20H), 1.14 (s, 6H), 1.14-1.12 (m, 2H), 0.70 (dd, J=3.9, 6.3 Hz, 2H). 13C NMR (CD3OD): δ=181.6, 179.0, 72.4, 43.2, 42.0, 38.6, 38.5, 35.2, 31.5, 31.2, 28.9, 26.94, 26.87, 26.3, 25.94, 25.92, 24.4, 13.67, 16.36. HRMS calcd for C19H35O5 (M+H)+: 343.2484, found 343.2487.

Workup

  1. stirringof stirring
  2. waitAfter 16 h
  3. extractionextracted with Et2O (3×50 mL)
  4. washThe combined organic phases were washed with brine (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-be42971bac87408bb05638b170a20674
Source dataset
uspto-grants-2008_07
Patent number
US07405226B2

Reaction notes

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