4-[2-(t-Butyldimethylsilanyloxy)ethoxymethyl]benzoic acid methyl ester → HCID 59678648, compound

HRID 1751840Notes

Reaction equation

HRID 1751840 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:6][CH:5]=1.[2H-].[Al+3].[Li+].[2H-].[2H-].[2H-]>>[Si:15]([O:14][CH2:13][CH2:12][O:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 596786884-[2-(t-Butyldimethylsilanyloxy)ethoxymethyl]benzoic acid methyl esterHCID 86600389Aluminum;lithium;deuteride

Product 1

HCID 59678648HCID 59678648, compoundYield 87.5%

Procedure

To a solution of the product of Example 8B (610 mg, 1.857 mmol) in THE (19 mL) at 0° C. was added a 1M solution (in THF) of lithium aluminum deuteride (1.9 mL, 1.857 mmol) dropwise. After completion of addition the ice bath was removed and the reaction was stirred at room temperature for 3.5 hours under nitrogen atmosphere, monitoring by TLC (3:1 pentane:ethyl acetate). The reaction was then diluted with water and extracted with ethyl acetate (2 times). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to obtain a clear oil (482 mg, 86% yield). The material was taken to the next step without further purification. 1H NMR (600 MHz, CDCl3): 7.33 (s, 4H), 4.56 (s, 2H), 0.89 (s, 9H), 0.06 (s, 6H).

Workup

  1. customwas removed
  2. additionThe reaction was then diluted with water
  3. extractionextracted with ethyl acetate (2 times)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee333918cd3b47c5a48804b922994378
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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