Tetrahydrofuran → (6-(Spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)methanol

HRID 2404097Notes

Reaction equation

HRID 2404097 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[CH2:21][CH2:20][C:19]4([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:18][CH2:17]3)[CH:11]=2)[CH:6]=1)=O.O1CCCC1.[AlH4-].[Li+]>>[CH2:20]1[C:19]2([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:18][CH2:17][CH:16]([O:15][C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[CH:6]=[C:5]([CH2:3][OH:2])[CH:14]=[CH:13]3)[CH2:21]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 28112Lithium aluminum hydrideHCID 66926514Methyl 6-(spiro[5.5]undecan-3-yloxy)-2-naphthoate

Product 1

HCID 66926446(6-(Spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)methanol

Procedure

To a solution of 6-(Spiro[5.5]undec-3-yloxy)-naphthalene-2-carboxylic acid methyl ester (0.374 g, 0.00106 mol) in tetrahydrofuran (10 mL, 0.1 mol) was added 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (3.18 mL, 0.00318 mol) at 0° C. The reaction was then allowed to warm to room temperature while stirring for 2 h, Rochele's salt was then added and stirred the resulting mixture was stirred at room temperature for 1 h. After extraction with ethyl acetate, and solvent removal under vacuum, (6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)methanol was obtained as a white solid (0.28 g, 83%). ESI-MS: 307.5 (M+H)+. 100%). 1H NMR (400 MHz, CDCl3) δ 7.74-7.70 (m, 3H), 7.44 (d, J=10.0 Hz, 1H), 7.16 (m, 2H), 4.81 (s, 2H), 4.40 (m, 1H), 1.94-1.26 (m, 18H).

Workup

  1. additionRochele's salt was then added
  2. stirringstirred the resulting mixture
  3. stirringwas stirred at room temperature for 1 h
  4. extractionAfter extraction
  5. customwith ethyl acetate, and solvent removal under vacuum

Sources & evidence

ORD record
ord-7c86151a966f450eaf13a1f2d882b886
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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