Water → HCID 22293544, compound

HRID 966976Notes

Reaction equation

HRID 966976 reaction equation
[C:1]1([C:7]2([CH:17]=[O:18])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][Mg]Br.[Cl-].[NH4+].O>O1CCCC1.C(OCC)(=O)C>[CH3:19][CH:17]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:15][CH2:16]1)[OH:18]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 122302758-phenyl-1,4-dioxaspiro[4,5]decane-8-carboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 22293544HCID 22293544, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-phenyl-1,4-dioxaspiro[4.5]decane-8-carboxaldehyde (J. Med. Chem. 1975, 18, 593-599; 4 g, 16.2 mmol) in tetrahydrofuran (100 mL) was added dropwise to a solution of methyl magnesium bromide (3.0M in ether, 8.1 mL, 24.3 mmol) in tetrahydrofuran (50 mL) at 0° C. The mixture was allowed to warm to room temperature over 4 hours, then aqueous ammonium chloride (saturated, 75 mL), water (75 mL) and ethyl acetate (100 mL) were added. The layers were separated and the organic fraction was dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (4.03 g, 96%). 1H NMR (360 MHz, CDCl3) δ 0.96 (3H, d, J 6.5 Hz), 1.12 (1H, br s), 1.40-1.66 (4H, m), 1.76-1.86 (2H, m), 2.24-2.28 (1H, m), 2.46-2.51 (1H, m), 3.61-3.64 (1H, m), 3.58-3.96 (4H, m), and 7.21-7.38 (5H, m).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic fraction was dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c3ca5519fc5c437d9de235f18602b80b
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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