Triethylamine → 4-[2-(Tert-butyl-dimethyl-silanyloxy)-ethyl]-2-fluoro-phenol

HRID 1036816Notes

Reaction equation

HRID 1036816 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][C:10]=1[F:18])C1C=CC=CC=1.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21].CCN(CC)CC>C(Cl)Cl>[C:20]([Si:23]([CH3:25])([CH3:24])[O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:18])[CH:11]=1)([CH3:22])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 672034892-(4-(Benzyloxy)-3-fluorophenyl)ethanol

Product 1

HCID 672032794-[2-(Tert-butyl-dimethyl-silanyloxy)-ethyl]-2-fluoro-phenolYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-benzyloxy-3-fluoro-phenyl)-ethanol (9.2 g, 37.4 mmol) in CH2Cl2 (150 mL) and TBDMS-Cl (5.6 g, 37.4 mmol), was added Et3N (5.2 mmol, 37.4 mmol) portionwise at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 hours at the same temperature. The reaction was washed with H2O (150 mL). The CH2Cl2 was dried over MgSO4 and concentrated under vacuum. To a solution of the residue in MeOH (100 mL), was Pd/C (150 mg) added. The reaction was stirred under H2 (1 atm) for 5 hours. The solid material was filtrated off and the filtrate was concentrated under vacuum to afford the desired compound (8.9 g, 88.3%) as a grayish solid. The crude compound was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.53 (s, 1H), 6.99˜6.96 (m, 1H), 6.83˜6.81 (m, 2H), 3.70 (t, 2H), 2.63 (t, 2H), 0.83 (s, 9H), 0.01 (s, 6H).

Workup

  1. washThe reaction was washed with H2O (150 mL)
  2. dry with materialThe CH2Cl2 was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. additionadded
  5. stirringThe reaction was stirred under H2 (1 atm) for 5 hours
  6. filtrationThe solid material was filtrated off
  7. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-87370273dc1144b6aa3c28b6d80b5db8
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

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