Ammonium Chloride → 6-Methoxy-2-p-methoxyphenyl-2-methyl-1-(6-tetrahydropyranyloxyhex-1-ynyl)-1,2,3,4-tetrahydronaphth-1-ol

HRID 1493301Notes

Reaction equation

HRID 1493301 reaction equation
C([Li])CCC.[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18].[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[C:27](=[O:31])[C:26]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)([CH3:32])[CH2:25][CH2:24]2.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[C:27]([C:18]#[C:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)([OH:31])[C:26]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)([CH3:32])[CH2:25][CH2:24]2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2821772-(Hex-5-yn-1-yloxy)tetrahydro-2h-pyranHCID 134065446-Methoxy-2-(4-methoxyphenyl)-2-methyltetraloneHCID 178418339Butyllithium

Product 1

HCID 198307706-Methoxy-2-p-methoxyphenyl-2-methyl-1-(6-tetrahydropyranyloxyhex-1-ynyl)-1,2,3,4-tetrahydronaphth-1-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyllithium (8.4 ml. of a 1.55 molar solution in hexane) was added to a solution of 6-tetrahydropyranyloxyhex-1-yne (2.25 g.) in tetrahydrofuran (25 ml.) at 10° C., the mixture was allowed to warm up to laboratory temperature and was stirred at that temperature for 30 minutes, and was then recooled to 10° C. A solution of 3,4-dihydro-6-methoxy-2-p-methoxyphenyl-2-methylnaphthalen-1(2H)-one (2.0 g.) in tetrahydrofuran (20 ml.) was added dropwise and the mixture was allowed to warm up to laboratory temperature and stirred at that temperature for 30 minutes. Saturated aqueous ammonium chloride solution (50 ml.) was added and the mixture was extracted with ethyl acetate. The extract was dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 3:1 v/v mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate as eluant. The product was crystallised from ethanol and there was thus obtained, as a mixture of isomers, 6-methoxy-2-p-methoxyphenyl-2-methyl-1-(6-tetrahydropyranyloxyhex-1-ynyl)-1,2,3,4-tetrahydronaphth-1-ol, m.p. 80°-82° C.

Workup

  1. temperatureto warm up to laboratory temperature
  2. customwas then recooled to 10° C
  3. temperatureto warm up to laboratory temperature
  4. stirringstirred at that temperature for 30 minutes
  5. extractionthe mixture was extracted with ethyl acetate
  6. customThe extract was dried
  7. customevaporated to dryness
  8. customthe residue was purified by chromatography on a silica gel column
  9. additiona 3:1 v/v mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate as eluant
  10. customThe product was crystallised from ethanol and there

Sources & evidence

ORD record
ord-205231bfea2d443ebd27736909b988e2
Source dataset
uspto-grants-1991_06
Patent number
US05021414

Reaction notes

Loading…