Hydrochloric Acid → 1-[9-(1-Carboxycyclopropyl)-5-hydroxynonyl]-1-cyclopropanecarboxylic acid

HRID 563155Notes

Reaction equation

HRID 563155 reaction equation
[C:1]([C:4]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]2([C:19]([OH:21])=[O:20])[CH2:18][CH2:17]2)[CH2:6][CH2:5]1)([OH:3])=[O:2].[OH-].[Na+].[BH4-].[Na+].Cl>CC(O)C.O>[C:19]([C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([OH:22])[CH2:10][CH2:9][CH2:8][CH2:7][C:4]2([C:1]([OH:3])=[O:2])[CH2:5][CH2:6]2)[CH2:17][CH2:18]1)([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 115440971-[9-(1-Carboxycyclopropyl)-5-oxononyl]-1-cyclopropanecarboxylic acid

Product 1

HCID 219320001-[9-(1-Carboxycyclopropyl)-5-hydroxynonyl]-1-cyclopropanecarboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a suspension of 1-[9-(1-carboxycyclopropyl)-5-oxononyl]-1-cyclopropanecarboxylic acid (6.95 g, 22.4 mmol) in iPrOH (40 mL) and H2O (40 mL) was added NaOH (1.80 g, 45.0 mmol). After 30 min of stirring, NaBH4 (0.45 g, 11.8 mmol) was added to the resulting clear solution. After 3 h and 15 min, the mixture was acidified to pH˜1 with aqueous HCl (1M) and extracted with Et2O (3×100 mL). The combined organic phases were dried (Na2SO4) and evaporated in vacuo to give 1-[9-(1-carboxycyclopropyl)-5-hydroxynonyl]-1-cyclopropanecarboxylic acid (6.02 g, 86%) as a slightly yellow oil. 1H NMR (CD3OD): δ=3.49 (br s, 1H), 1.57-1.25 (m, 16H), 1.14 (dd, J=3.6, 6.3, 4H), 0.70 (dd, J=3.3, 6.3, 4H). 13C NMR (CD3OD): δ=178.9 (2×), 72.2, 38.4 (2×), 35.1 (2×), 28.9 (2×), 27.0 (2×), 24.3 (2×), 16.3 (2×), 16.2 (2×).

Workup

  1. waitAfter 3 h
  2. custom15 min
  3. extractionextracted with Et2O (3×100 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-499abe8c1c004f1eaf1dd30c0a3908f5
Source dataset
uspto-grants-2011_11
Patent number
US08067466B2

Reaction notes

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