Water → 5-(3,7-Dimethylocta-2,6-dienyl)-7,8-dimethylspiro[chroman-2,1'-cyclobutan]-6-ol

HRID 2103040Notes

Reaction equation

HRID 2103040 reaction equation
[CH3:1][C:2]1[C:14]([CH3:15])=[C:13]2[C:5]([CH2:6][CH2:7][C:8]3([O:12]2)[CH2:11][CH2:10][CH2:9]3)=[CH:4][C:3]=1[OH:16].[CH3:17][C:18](=[CH:20][CH2:21][CH2:22]/[C:23](=[CH:25]/[CH2:26]O)/[CH3:24])[CH3:19].O>O1CCOCC1>[CH3:24][C:23]([CH2:22][CH2:21][CH:20]=[C:18]([CH3:19])[CH3:17])=[CH:25][CH2:26][C:4]1[C:3]([OH:16])=[C:2]([CH3:1])[C:14]([CH3:15])=[C:13]2[C:5]=1[CH2:6][CH2:7][C:8]1([O:12]2)[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 637566GeraniolHCID 578034927,8-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol

Product 1

HCID 690568075-(3,7-Dimethylocta-2,6-dienyl)-7,8-dimethylspiro[chroman-2,1'-cyclobutan]-6-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7,8-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (0.5 g) in 20 mL of dioxane under argon, was added borontrifluoride-diethyl etherate (0.72 mL) followed by geraniol (0.4 mL) and the reaction was stirred overnight. After addition of water, the solution was extracted with EtOAc, washed with brine, dried over Na2SO4, and evaporated. The residue was purified on a silica column eluting with 1:8 EtOAc/hexane to give 5-(3,7-dimethylocta-2,6-dienyl)-7,8-dimethylspiro[chroman-2,1′-cyclobutan]-6-ol (104 mg ) as an amber oil. 1H-NMR (300 MHz, CDCl3) δ=1.65-1.99 (m, 10H), 2.01-2.28 (m, 17H), 2.74-2.79 (t, 2H), 3.35-3.37 (d, H), 4.78 (s, 1H), 5.10-5.12 (t, 1H), 5.17-5.21 (t, 1H) ppm. 13C-NMR (75 MHz, CDCl3) δ=11.93, 12.15, 12.61, 16.21, 17.80, 20.47, 25.55, 25.80, 26.45, 29.58, 34.05, 39.74, 76.23, 117.15, 121.87, 121.97, 122.48, 123.62, 123.89, 132.02, 138.03, 145.52, 145.89 ppm. MS (m/z)=354 (M+H+).

Workup

  1. extractionthe solution was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified on a silica column
  6. washeluting with 1:8 EtOAc/hexane

Sources & evidence

ORD record
ord-a3d895e60fc54dcdae9883c76ae6fd03
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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