Hydrochloric Acid → HCID 59858090, compound

HRID 2378378Notes

Reaction equation

HRID 2378378 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]4[CH2:16][CH:12]([CH2:13][CH2:14]4)[C:11]=13)[O:8][C:7]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:17])[CH2:6][CH2:5]2.[OH-].[Na+].[CH2:25](Br)[CH:26]=[C:27]([CH3:29])[CH3:28].Cl>CCOC(C)=O>[OH:1][C:2]1[C:3]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])=[C:4]2[C:9](=[C:10]3[CH:15]4[CH2:16][CH:12]([CH2:13][CH2:14]4)[C:11]=13)[O:8][C:7]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])([CH3:17])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-HCID 11609154HCID 11609154, compound

Product 1

HCID 59858090HCID 59858090, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid, (2.39 mmol) in 1M aq. NaOH (4.8 mL, 4.8 mmol) was cooled to 0° C., and treated with prenyl bromide (0.277 mL, 2.39 mmol). Following stirring for 7 h at ambient temperature the reaction mixture was made slightly acidic with 0.5M HCl and shaken with EtOAc. The organic phase was evaporated yielding 1. The mixture was subjected to column chromatography on silica gel (SiO2: hexane:EtOAc, 85:15 v/v eluting yielded 3-[6-hydroxy-2-methyl-5-(3-methyl-but-2-enyl)-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl]-propionic acid 1H-NMR (300 MHz, CDCl3) δ (ppm): 5.17 (t, J=6, 1H), 3.54 (br s, 1H), 3.49 (br s, 1H), 3.18-3.37 (m, 2H), 2.70 (t, J=7, 2H), 2.49-2.62 (m, 2H), 1.60-2.07 (m, 13H), 1.39-1.48 (m, 1H), 1.05-1.32 (m, 5H). 13C-NMR (75 MHz CDCl3) δ (ppm): 180.1, 141.1, 133.9, 133.3, 132.9, 122.9, 122.3, 117.4, 73.2, 49.0, 48.9, 40.0, 39.8, 33.6, 32.0, 28.7, 26.7, 25.9, 25.6, 23.8, 233.2, 20.5, 18.0. MS ESI-Pos m/z371.2 (M+H+)

Workup

  1. customThe organic phase was evaporated
  2. customyielding 1
  3. washhexane:EtOAc, 85:15 v/v eluting

Sources & evidence

ORD record
ord-64c69d1a2b434ae2953e247ee80174cb
Source dataset
uspto-grants-2008_12
Patent number
US07470798B2

Reaction notes

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