Water → HCID 66617066, compound

HRID 455777Notes

Reaction equation

HRID 455777 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([CH3:39])([CH3:38])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([O:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:30])([CH3:29])[C:24](OCC)=[O:25])C.O.[OH-].[Na+]>CC(OC)(C)C>[CH3:38][C:11]([CH3:39])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([O:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([CH3:29])([CH3:30])[CH2:24][OH:25])[CH2:10][OH:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66617162HCID 66617162, compound

Product 1

HCID 66617066HCID 66617066, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Under nitrogen atmosphere, LiAlH4 (2.2 g, 58 mmol) was suspended in anhydrous MTBE (250 mL) and cooled with an ice/water bath. 2,2,14,14-Tetramethyl-8-(tetrahydropyran-2-yloxy)-pentadecanedioic acid diethyl ester (12.0 g, 24.7 mmol) in anhydrous MTBE (100 mL) was added dropwise over 1.5 h. This mixture was left overnight at ambient temperature. After the reaction was completed, deionized water (4 mL) was added followed by 20% aqueous NaOH solution (5 mL) and water (14 mL). The ether solution was decanted from the formed white residue. The residue was washed with MTBE (4×20 mL) and the combined ether solutions were dried over MgSO4. The solvent was removed under reduced pressure to give crude 2,2,14,14-tetramethyl-8-(tetrahydropyran-2-yloxy)-pentadecane-1,15-diol as a colorless oil (8.9 g, 90%), which was used without further purification. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 4.72-4.59 (m, 1H), 4.03-3.84 (m, 1H), 3.69-3.38 (m, 2H), 3.31 (s, 4H), 2.00-1.15 (m, 28H), 0.87 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 97.38, 76.57, 71.83, 62.65, 38.55, 34.96, 34.84, 33.33, 31.17, 30.75, 30.63, 26.92, 25.52, 24.95, 23.84, 23.70, 19.96. HRMS (EI, POS): Calcd for C24H48O4 (M+): 400.3553. found: 400.3564.

Workup

  1. temperaturecooled with an ice/water bath
  2. customThe ether solution was decanted from the formed white residue
  3. washThe residue was washed with MTBE (4×20 mL)
  4. dry with materialthe combined ether solutions were dried over MgSO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a2461bfe53c342169fa12152753c6897
Source dataset
uspto-grants-2013_07
Patent number
US08497301B2

Reaction notes

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