Hydrochloric Acid → HCID 11609154, compound

HRID 254237Notes

Reaction equation

HRID 254237 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-ee5f31b4a032497e89d12a8a214ce729
Source dataset
uspto-grants-2011_01
Patent number
US07875607B2

Reaction notes

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