Hydrochloric Acid → HCID 131714173, compound

HRID 1381161Notes

Reaction equation

HRID 1381161 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[O:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[C@@H:10]2[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]3)[CH:6]=[CH:7][CH:8]=1.C[S-].[Li+].Cl>CN(C)P(N(C)C)(N(C)C)=O.O>[OH:2][C:3]1[CH:4]=[C:5]([C@@:9]23[O:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[C@@H:10]2[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]3)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11018798HCID 11018798, compoundHCID 131714174HCID 131714174, compound

Product 1

HCID 131714173HCID 131714173, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 3.50 g of cis-1,2,3,4,4a,9b-hexahydro-4a-(3-methyoxyphenyl)-2-methyl-benzofuro[3,2-c]pyridine and 3.62 g of lithium thiomethoxide in 30 ml of dry hexamethylphosphoramide was heated at 140° under a drying tube for 41/2 hours. The cooled reaction mixture was diluted with 350 ml of water and the pH adjusted to 7 by slow addition of 2N HCl with stirring. The mixture was extracted with ether (2×300), and the combined extracts were washed with water (3×300 ml), dried over anhydrous Na2SO4, and evaporated in vacuo to provide 3.16 g (94.8%) a solid foam. This material was boiled and triturated with a small amount of ether. After cooling to 0°, the resulting solid was filtered off, washed with cold ether, and dried to afford 2.58 g (77.4%) of crystalline solid, m.p. s 157, 158°-160°.

Workup

  1. temperaturewas heated at 140° under a drying tube for 41/2 hours
  2. customThe cooled reaction mixture
  3. extractionThe mixture was extracted with ether (2×300)
  4. washthe combined extracts were washed with water (3×300 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-32a0712ed36846888f25ead2f85262b1
Source dataset
uspto-grants-1986_04
Patent number
US04585779

Reaction notes

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