3-Bromo-1-propanol → HCID 9837801, compound

HRID 1840510Notes

Reaction equation

HRID 1840510 reaction equation
[C:1]([S:4][CH2:5][C:6]1([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)(=O)[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].BrCC[CH2:29][OH:30]>CO>[OH:30][CH2:29][CH2:2][CH2:1][S:4][CH2:5][C:6]1([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 23448262Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylate

Product 1

HCID 9837801HCID 9837801, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of Intermediate 7 (2.50 g) in methanol (100 ml) under nitrogen at 0° C. was added a solution of sodium hexamethyldisilazide (1M in THF, 11.3 ml) and the resulting mixture was stirred for 10 mins, then a solution of 3-bromopropanol (1.5 g) was added. The mixture was stirred for 6 h, then evaporated and the residue treated with water (100 ml) and extracted with dichloromethane (4×50 ml). The combined dichloromethane extracts were washed with water (2×50 ml), brine (50 ml), dried over MgSO4 and evaporated. The residue was purified on silica gel eluting with 2:1 ethyl acetate/hexane, to give the title compound (2.41 g) as a colourless oil. TLC Rf0.26 (2:1 ethyl acetate/hexane).

Workup

  1. stirringThe mixture was stirred for 6 h
  2. customevaporated
  3. additionthe residue treated with water (100 ml)
  4. extractionextracted with dichloromethane (4×50 ml)
  5. washThe combined dichloromethane extracts were washed with water (2×50 ml), brine (50 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified on silica gel eluting with 2:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-07b92c995efc4844a76f3cf138b4b1ce
Source dataset
uspto-grants-2004_01
Patent number
US06680338B2

Reaction notes

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