Water → 3-Formyl-1,5-bis(tert-butyldimethylsilyloxy)pentane

HRID 420439Notes

Reaction equation

HRID 420439 reaction equation
[C:1]([CH:3]([CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:4][CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])#N.CC(C[AlH]CC(C)C)C.[OH2:33].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:1]([CH:3]([CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:4][CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[O:33]

Participants

6

Reactant 4

HCID 962Water2×HCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 142934823-Cyano-1,5-bis(tert-butyldimethylsilyloxy)pentane

Product 1

HCID 142934833-Formyl-1,5-bis(tert-butyldimethylsilyloxy)pentaneYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following a published procedure,24 a solution of 3 (3.65 g, 10.2 mmol) in dry toluene (52 mL) at −78° C. under argon was treated with DIBALH (12 mmol, 8.3 mL, 1.5 M solution in toluene), and the reaction was allowed to proceed for 1 h. Water (2.6 mL) was added, and the mixture was allowed to reach room temperature. Aqueous NaOH (2.6 mL, 4.0 M solution) was added, and stirring was continued for 15 min. Water (7.8 mL) was added and the suspension was stirred for a further 15 min. The sample was dried (Na2SO4), concentrated at reduced pressure, and chromatographed [silica, petroleum ether/diethyl ether (20:1)], affording a colorless liquid (2.70 g, 73%): IR (film, νmax cm−1) 2955, 2859, 1729, 1708, 1472; 1H NMR δ 0.01 (s, 12H), 0.87 (s, 18H), 1.64-1.74 (m, 2H), 1.85-1.96 (m, 2H), 2.50 (m, 1H), 3.57-3.68 (m, 4H), 9.65 (d, J=2.4 Hz, 1H); 13C NMR δ −5.27, 18.45, 26.09, 32.15, 46.40, 60.80, 204.74; EI-MS 171/172, 141, 97, 75, calcd 360.2516 (C18H40O3Si2); Anal. Calcd C, 59.94; H, 11.18. Found: C, 58.15; H, 11.16.

Workup

  1. customat −78° C.
  2. customto reach room temperature
  3. waitwas continued for 15 min
  4. stirringthe suspension was stirred for a further 15 min
  5. dry with materialThe sample was dried (Na2SO4)
  6. concentrationconcentrated at reduced pressure
  7. customchromatographed [silica, petroleum ether/diethyl ether (20:1)]

Sources & evidence

ORD record
ord-58e5571c8ce84f719e36f40325b5c39b
Source dataset
uspto-grants-2012_01
Patent number
US08097609B2

Reaction notes

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