Tetrahydrofuran → 6-(spiro[4.5]Dec-8-yloxy)-2-naphthalenemethanol

HRID 2404215Notes

Reaction equation

HRID 2404215 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH:16]3[CH2:25][CH2:24][C:19]4([CH2:23][CH2:22][CH2:21][CH2:20]4)[CH2:18][CH2:17]3)[CH:11]=2)[CH:6]=1)=O.O1CCCC1>[AlH4-].[Li+]>[CH2:20]1[C:19]2([CH2:24][CH2:25][CH:16]([O:15][C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][CH:9]=3)[CH:6]=[C:5]([CH2:3][OH:2])[CH:14]=[CH:13]4)[CH2:17][CH2:18]2)[CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 66926552HCID 66926552, compound

Product 1

HCID 669264716-(spiro[4.5]Dec-8-yloxy)-2-naphthalenemethanolYield 90%

Reagents, catalysts & solvents 1

HCID 28112Lithium aluminum hydrideSolvent

Procedure

6-(Spiro[4.5]dec-8-yloxy)-naphthalene-2-carboxylic acid methyl ester (0.312 g, 0.000922 mol) in tetrahydrofuran (9 mL, 0.1 mol) and 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (2.76 mL, 0.00276 mol) was added at 0° C. After stirring at rt for 2 h, quench with EtOAc, then Rochele's salt was added and stirred at rt for 1 h. Extraction with EtOAc, c/c give the product as a white solid (257.2 mg, 90%). LCMS Rt=2.21 min m/z=293.30 ([M-17], 100%).

Workup

  1. customquench with EtOAc
  2. additionRochele's salt was added
  3. stirringstirred at rt for 1 h
  4. extractionExtraction with EtOAc, c/c

Sources & evidence

ORD record
ord-b8daa650f8954b7086e8491b5f7bebfd
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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