Sodium Methoxide → 7,8-Dimethyl-5[(Z)-2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1'-cyclobutan]-6-ol

HRID 2103039Notes

Reaction equation

HRID 2103039 reaction equation
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)C=CC=CC=1.C[O-].[Na+].[OH:35][C:36]1[C:48]([CH3:49])=[C:47]([CH3:50])[C:46]2[O:45][C:41]3([CH2:44][CH2:43][CH2:42]3)[CH2:40][CH2:39][C:38]=2[C:37]=1[CH:51]=O>C1COCC1>[CH3:49][C:48]1[C:47]([CH3:50])=[C:46]2[C:38]([CH2:39][CH2:40][C:41]3([O:45]2)[CH2:42][CH2:43][CH2:44]3)=[C:37](/[CH:51]=[CH:9]\[C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[C:36]=1[OH:35]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 23163315Triphenyl[(quinolin-2-yl)methyl]phosphanium bromideHCID 866054866-Hydroxy-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-5-carbaldehyde

Product 1

HCID 1363641377,8-Dimethyl-5[(Z)-2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1'-cyclobutan]-6-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

MS (m/z)=404 (M+H+). To a suspension of 0.35 g of triphenyl(quinolin-2-ylmethyl)phosphonium bromide in 5 mL of THF was added 3 mL of 0.5 M sodium methoxide at 0° C under Argon, followed by a solution of 6-Hydroxy-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-5-carbaldehyde 0.18 g) in 10 mL of THF. The solution was stirred for 1 hr at 0° C., warmed to room temperature, and stirred for 2 hrs. The tetrahydrofuran was evaporated, and the residue was partitioned between EtOAc and H2O, washed with brine, then dried over Na2SO4. The crude material was purified on a silica column eluting with 1:8 EtOAc/Hexane. 50 mg of 7,8-dimethyl-5-[2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1′-cyclobutan]-6-ol which was precipitated with hexane. 1H-NMR (300 MHz, CDCl3) δ=1.70-1-76 (m, 3H), 1.78-1.97 (m, 5H), 2.09-2.30 (m, 8H), 2.81-2.85 (t, 2H), 5.70 (brs, 1H), 7.18-7.24 (d, 1H), 7.50-7.56 (m, 2H), 7.71-7.82 (m, 3H), 8.08-8.13 (m, 2H) ppm. 13C-NMR (75 MHz, CDCl3) δ=12.24, 12.34, 12.60, 21.25, 29.31, 34.10, 76.51, 117.47, 119.17, 119.65, 112.33, 126.29, 126.46, 127.45, 127.55, 129.23, 129.88, 130.01, 133.47, 136.49, 145.10, 155.55 ppm. MS (m/z)=372 (M+H+).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 2 hrs
  3. customThe tetrahydrofuran was evaporated
  4. customthe residue was partitioned between EtOAc and H2O
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe crude material was purified on a silica column
  8. washeluting with 1:8 EtOAc/Hexane
  9. custom50 mg of 7,8-dimethyl-5-[2-quinolin-2-ylvinyl] 3,4-dihydrospiro-[chromene-2,1′-cyclobutan]-6-ol which was precipitated with hexane

Sources & evidence

ORD record
ord-50b2db4e5fca4dc6ae65d2f1da1cfae1
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…