Sodium borohydride → HCID 85986802, compound

HRID 1466713Notes

Reaction equation

HRID 1466713 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:25])[CH2:12][CH2:13][CH2:14][C:15]([CH3:24])([CH3:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:2].[BH4-].[Na+]>C(O)(C)C.O>[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:26])([CH3:27])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:25])[CH2:12][CH2:13][CH2:14][C:15]([CH3:24])([CH3:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 85986804HCID 85986804, compound

Product 1

HCID 85986802HCID 85986802, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2,2,12,12-tetramethyl-8-oxopentadecanedioic acid diethyl ester (33.6 g, 84.3 mmol) in 60% aqueous isopropanol (337 mL) was added sodium borohydride (1.6 g, 41 mmol). The reaction mixture was heated to 45° C. for 2 h, diluted with water (400 mL), and extracted with MTBE (2×200 mL). The combined organic layers were washed with water (200 mL), dried over sodium sulfate, and concentrated in vacuo to give the crude product (33.0 g, 98%). 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 4.11 (q, J=7.2 Hz, 4H), 3.55-3.45 (m, 1H), 1.60-1.18 (m, 26H), 1.15 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 178.1, 72.0, 60.3, 42.4, 40.9, 37.7, 30.4, 25.8, 25.4, 25.1, 14.5. HPLC: 87.5% pure.

Workup

  1. extractionextracted with MTBE (2×200 mL)
  2. washThe combined organic layers were washed with water (200 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-879d1a3db0634f0eae50537a2998b970
Source dataset
uspto-grants-2015_04
Patent number
US09000041B2

Reaction notes

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