Sodium Hydroxide → HCID 11218203, compound

HRID 899657Notes

Reaction equation

HRID 899657 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11](=[CH2:22])[CH2:12][O:13]C(=O)C1C=CC=CC=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OCC(=C)CCOC(=O)C1C=CC=CC=1)(C(C)(C)C)(C)C.[OH-].[Na+]>CO.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[Si:1]([O:8][CH2:9][CH2:10][C:11](=[CH2:22])[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 86590315HCID 86590315, compoundHCID 131726818HCID 131726818, compound

Product 1

HCID 11218203HCID 11218203, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To an ˜7:1 mixture of benzoic acid 4-(tert-butyldimethylsilyloxy)-2-methylene-butyl ester and benzoic acid 3-(tert-butyldimethylsilyloxymethyl)-but-3-enyl ester (1.00 g, 3.13 mmol) in methanol (31 mL) was added NaOH (0.306 g, 7.64 mmol) and the mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (75 mL) and saturated aqueous NaHCO3 (20 mL). The phases were separated and the organic phase was washed with brine (2×10 mL), dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (9:1 hexanes-ethyl acetate) provided 0.58 g (58%) of 4-(tert-butyldimethylsilyloxy)-2-methylene-butan-1-ol as a colorless oil. 1H NMR (CDCl3) δ 0.06 (s, 6H), 0.90 (s, 9H), 2.34 (t, 2H, J=6.0 Hz); 2.78 (br s, 1H), 3.75 (t, 2H, J=6.0 Hz), 4.07-4.11 (m, 2H), 4.90 (s, 1H), 5.04 (s, 1H);

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (9:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-ad647748a1044540a5ccfcc5efc54387
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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