Methanol → HCID 86690731, compound

HRID 1473914Notes

Reaction equation

HRID 1473914 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][C:13](OC(C)(C)C)=[O:14])[C:5]=2[CH2:4][O:3]1.[Li+].[BH4-].CO>C1COCC1>[CH3:1][C:2]1([CH3:20])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 4148881Lithium borohydrideHCID 86690732HCID 86690732, compound

Product 1

HCID 86690731HCID 86690731, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)acetate (2.6 g, 80% pure, 9.34 mmol, 1 eq.) in THF (20 mL) were added LiBH4 (7.0 mL, 14.01 mmol, 1.5 eq.) and MeOH (1.0 mL) at rt. The mixture was stirred at rt for 30 min, added MeOH (20 mL), concentrated to dryness, added MeOH (20 mL) and silica gel, and concentrated to dryness again. The mixture was loaded directly on silica gel for purification using a mixture of EtOAc and hexanes as eluent to give 2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)ethanol (1.1 g, 71%) as a pale brown oil. 1H NMR (400 MHz, CDCl3) δ 7.28 (t, J=7.9 Hz, 1H), 6.92 (d, J=7.4 Hz, 1H), 6.86 (d, J=8.2 Hz, 1H), 5.02 (s, 2H), 3.99 (q, J=6.4 Hz, 2H), 2.86 (t, J=6.6 Hz, 2H), 1.68 (s, 6H), 1.57 (t, J=5.5 Hz, 1H).

Workup

  1. concentrationconcentrated to dryness
  2. additionadded MeOH (20 mL) and silica gel
  3. concentrationconcentrated to dryness again
  4. customThe mixture was loaded directly on silica gel for purification
  5. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-819206349c1d4671a2886078cee5a757
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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