Hydrochloric Acid → HCID 57871414, compound

HRID 550207Notes

Reaction equation

HRID 550207 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([C:27]([OH:29])=[O:28])[CH:21]=[CH:20]3)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:30].[BH4-].[Na+].Cl>C1COCC1>[CH2:13]([C:12]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([C:27]([OH:29])=[O:28])[CH:21]=[CH:20]2)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:31])[C:2]([CH3:32])([CH3:33])[CH3:1])=[C:7]([CH3:30])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 11554132HCID 11554132, compound

Product 1

HCID 57871414HCID 57871414, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of 6-{1-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carboxylic acid (0.15 g, 0.34 mmol) in THF (6 mL) with NaBH4 (0.025 g, 0.67 mmol) and stir the reaction mixture at RT for 1 h. Quench the reaction first with water (5 mL) and then with 1N HCl (2 mL). Remove the THF under vacuum. Dilute the mixture with EtOAc (50 mL), wash with brine (2×), dry over NaSO4 and filter. Concentrate the filtrate to give the title compound (0.15 g). MS (ES) m/e 447 (M−1).

Workup

  1. customQuench
  2. customthe reaction first with water (5 mL)
  3. customRemove the THF under vacuum
  4. additionDilute the mixture with EtOAc (50 mL)
  5. washwash with brine (2×)
  6. dry with materialdry over NaSO4
  7. filtrationfilter
  8. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-e28b03ddbbd54c9f935f98a198643023
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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