HCID 66959976, compound → HCID 66960256, compound

HRID 1367740Notes

Reaction equation

HRID 1367740 reaction equation
C([O:8][C:9]1[C:10]([O:38][CH3:39])=[CH:11][C:12]2[CH:13]3[CH:21]([CH2:22][CH2:23][C:24]=2[CH:25]=1)[CH:20]1[C:16]([CH3:37])([CH:17]([O:26][CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:18][CH2:19]1)[CH2:15][CH2:14]3)C1C=CC=CC=1>C1COCC1.[Pd]>[C:33]([Si:30]([CH3:32])([CH3:31])[O:29][CH2:28][CH2:27][O:26][CH:17]1[C:16]2([CH3:37])[CH:20]([CH:21]3[CH:13]([CH2:14][CH2:15]2)[C:12]2[CH:11]=[C:10]([O:38][CH3:39])[C:9]([OH:8])=[CH:25][C:24]=2[CH2:23][CH2:22]3)[CH2:19][CH2:18]1)([CH3:36])([CH3:35])[CH3:34]

Participants

4

Reactant 1

HCID 66959976HCID 66959976, compound

Product 1

HCID 66960256HCID 66960256, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred, degassed, solution of ether 46 (200 mg, 0.36 mmol) in THF (10 mL) was treated with 10% Pd/C (20 mg) and placed under an atmosphere of hydrogen overnight. The reaction was then filtered through celite and evaporated to give the desired phenol 47 as a clear colourless oil δH 6.80 (1H, s, ArH), 6.65 (1H, s, ArH), 5.55 (1H, s, OH), 3.87 (3H, s, OMe), 3.52-3.82 (4H, m, 2×OCH2), 3.42-3.48 (1H, m, 17-CH), 2.72-2.84 (2H, m, 6-CH2), 1.20-2.36 (13H, m), 0.94 (9H, s, tBu), 0.89 (3H, s, 18-Me) and 0.12 (6H, s, SiMe2).

Workup

  1. customA stirred, degassed
  2. filtrationThe reaction was then filtered through celite
  3. customevaporated

Sources & evidence

ORD record
ord-50784c3bb42d4fd7a2e208fd4267d26d
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

Loading…