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

HRID 1690876Notes

Reaction equation

HRID 1690876 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-cc911a6453f14e18843d1ca299b09578
Source dataset
uspto-grants-2012_04
Patent number
US08153690B2

Reaction notes

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