Ammonium Chloride → 1-(4-(((4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)phenyl)prop-2-en-1-ol

HRID 536776Notes

Reaction equation

HRID 536776 reaction equation
[CH2:1]([C@H:8]1[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@@H:9]1[CH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH:24]([Mg]Br)=[CH2:25].[NH4+].[Cl-]>C1COCC1>[CH2:1]([C@H:8]1[O:12][C:11]([CH3:13])([CH3:14])[O:10][C@@H:9]1[CH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]([OH:21])[CH:24]=[CH2:25])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58560719HCID 58560719, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 585606871-(4-(((4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)phenyl)prop-2-en-1-olYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(((4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)benzaldehyde (N) (15.5 mg, 0.048 mmol) in THF (1.2 mL) at 0° C. was added vinylmagnesium bromide (55 μL, 1M in THF) dropwise. After 30 minutes, saturated aqueous NH4Cl was added at 0° C., and the mixture was extracted with ether. The collected organic layers were washed with brine, dried with MgSO4, filtered and concentrated to yield the title compound (12.1 mg, 0.035 mmol, 72%). 1H NMR (CDCl3, 300 MHz) δ 7.36-7.22 (4H, m), 6.10-5.99 (1H, m), 5.34 (1H, d, J=17.1 Hz), 5.20-5.17 (2H, m), 3.88-3.81 (1H, m), 3.71-3.65 (1H, m), 2.95-2.84 (2H, m), 1.51-1.29 (12H, m), 1.37 (3H, s), 1.35 (3H, s), 0.88 (3H, t, J=4.8 Hz); LRMS (APCI+) calcd for C22H35O3 [M−H]: 345.2; found 345.4.

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe collected organic layers were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c7e9a11efa0452899647f1893fefc60
Source dataset
uspto-grants-2014_10
Patent number
US08859615B2

Reaction notes

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