6-Methoxy-alpha-tetralone → 1,2,3,4-Tetrahydro-2-naphthalenol

HRID 1529842Notes

Reaction equation

HRID 1529842 reaction equation
C([Mg]Br)=C.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=O)[CH2:12][CH2:11][CH2:10]2.[NH4+].[Cl-]>C1COCC1>[CH2:16]1[CH:7]([OH:6])[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15]1

Participants

5

Reactant 3

HCID 141126-Methoxy-alpha-tetraloneHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 107471,2,3,4-Tetrahydro-2-naphthalenolYield 127.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of vinylmagnesium bromide (1.0 M in THF, 1700 mL) was transferred in a 12 L 3-neck round bottom flask fitted with a thermocouple probe, a 2 L dropping funnel, an inlet argon, and a mechanical stirrer. At rt, a solution of 6-methoxy-1-tetralone (250 g, 1.42 mol) in 830 mL of THF was added dropwise over a period of 2.5 h, maintaining the internal temperature below 30° C. The mixture was stirred at rt for 0.5 h. At rt, a solution of saturated aqueous NH4Cl (1 L) was slowly added by maintaining the internal temperature below 30° C. The THF was decanted and rotary concentrated. The residual aqueous phase was extracted with ethyl acetate (3×1 L). The combined organic phase was washed with brine, dried over magnesium sulfate and rotary evaporated to give 269 g (93%) of crude tetralol 46. 1H NMR (400 MHz, CDCl3) δ 1.80-2.05 (m, 4H), 2.70-2.90 (m, 2H), 3.81 (s, 3H), 5.21 (d, J=10.6 Hz, 1H), 5.33 (d, J=17.1 Hz, 1H), 6.04 (dd, J1=17.1 Hz, J2=10.6 Hz, 1H), 6.64 (m, 1H), 6.77 (m, 1H), 7.32 (d, J=8.6 Hz, 1H) ppm (described in Tetrahedron, 18, 1355 (1962)).

Workup

  1. customfitted with a thermocouple probe
  2. temperaturemaintaining the internal temperature below 30° C
  3. temperatureby maintaining the internal temperature below 30° C
  4. customThe THF was decanted
  5. extractionThe residual aqueous phase was extracted with ethyl acetate (3×1 L)
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customrotary evaporated

Sources & evidence

ORD record
ord-601da1d69f644d5d848602d72782f7c3
Source dataset
uspto-grants-2015_07
Patent number
US09090651B2

Reaction notes

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