Hydrochloric Acid → HCID 11609154, compound

HRID 2378370Notes

Reaction equation

HRID 2378370 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1([CH3:22])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([OH:16])[CH:12]=2)[O:7]1.[OH-].[Na+].O1CCOCC1.Cl>C(OCC)(=O)C.O>[OH:16][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]=13)[O:7][C:6]([CH2:5][CH2:4][C:3]([OH:23])=[O:2])([CH3:22])[CH2:15][CH2:14]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 11716671HCID 11716671, compound

Product 1

HCID 11609154HCID 11609154, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 gram (3.16 mmol) of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester, prepared as described in Example 13, was mixed with 20 mL of 2N NaOH and 20 mL of dioxane, the mixture was stirred for 5 hours and was acidified with dilute HCl. Water and ethyl acetate were added and the organic layer was separated, washed and dried over MgSO4. After the removal of solvents, the residue was further purified by flash column chromatography on silica gel (3:2 ethyl acetate/hexane) to afford 700 mg of 3-(6-hydroxy-2-methyl-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): 6.29 (s, 1H), 4.70 (s, 1H), 3.52-3.46 (d, 2H), 2.69-2.55 (m, 2H), 2.52-2.47 (m, 2H), 2.00-1.64 (m, 8H), 1.43-1.15 (m,5H); MS: 302 (M+H+, 73%), 325 (M+Na+, 100%).

Workup

  1. customthe organic layer was separated
  2. washwashed
  3. dry with materialdried over MgSO4
  4. customAfter the removal of solvents
  5. customthe residue was further purified by flash column chromatography on silica gel (3:2 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e4370981241248a5929cb401da5b73e7
Source dataset
uspto-grants-2008_12
Patent number
US07470798B2

Reaction notes

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