Acetic Acid → Benzyl 4-hydroxy-1H-indole-1-carboxylate

HRID 16569

Reaction equation

HRID 16569 reaction equation
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 11703628Benzyl 4-(t-butyldimethylsilyloxy)indole-1-carboxylate

Product 1

HCID 12622101Benzyl 4-hydroxy-1H-indole-1-carboxylateYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 10 (28.62 g, 75 mmol) in tetrahydrofuran (375 mL) containing acetic acid (4.5 g, 75 mmol) was treated at 0° C. with 1 M tetrabutylammonium fluoride (75 mL, 75 mmol) and the mixture was stirred at 0° C. for 40 min. The solvent was evaporated and the residue was dissolved in diethyl ether (250 mL) and washed with saturated aq. sodium bicarbonate and brine, dried and evaporated to give a brown solid which was washed with cold hexanes to give 11 as white fluffy needles (14.13 g, 70%), mp 118-120° C. (from dichloromethane-hexanes), (lit.11 mp 121-124° C.).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in diethyl ether (250 mL)
  3. washwashed with saturated aq. sodium bicarbonate and brine
  4. customdried
  5. customevaporated
  6. customto give a brown solid which
  7. washwas washed with cold hexanes

Sources & evidence

ORD record
ord-7b6517d98c05498aa1c66ec4e8f2faff
Source dataset
uspto-grants-2010_06
Patent number
US07737169B2

Linked notes

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