Water → HCID 54490045, compound

HRID 2256817Notes

Reaction equation

HRID 2256817 reaction equation
[C:1]([O:20][CH2:21][CH:22]([CH2:25][CH2:26][OH:27])[CH2:23][OH:24])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:33][CH3:34])CC)C.[C:35](Cl)(=[O:37])[CH3:36].[OH2:39]>C(OCC)C>[C:35]([O:24][CH2:23][CH:22]([CH2:21][O:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:25][CH2:26][O:27][C:33](=[O:39])[CH3:34])(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19027592HCID 19027592, compound

Product 1

HCID 54490045HCID 54490045, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of 2-trityloxymethyl-1,4-butandiol (50.85 g, 0.140 mol) and triethylamine (42.6, 0.42 mol) in dry diethyl ether (500 ml) was added slowly a solution of acetyl chloride (27.5 g, 0.35 mol) in ether (25 ml) with external cooling with cold water to maintain room temperature in the mixture. After 45 min the triethylamine hydrochloride was filtered off and washed with a little ether. The combined filtrate was washed with water (50 ml), 0.5M hydrochloric acid (100 mi) and water (50 ml), dried with magnesium sulfate and evaporated in vacuum, finally at 0.1 mBar, to give 61.03 g (97%) of crude oily product. TLC on silica (ethyl acetate+n-hexane 1+1): Rf 0.68.

Workup

  1. filtrationAfter 45 min the triethylamine hydrochloride was filtered off
  2. washwashed with a little ether
  3. washThe combined filtrate was washed with water (50 ml), 0.5M hydrochloric acid (100 mi) and water (50 ml)
  4. dry with materialdried with magnesium sulfate
  5. customevaporated in vacuum, finally at 0.1 mBar
  6. customto give 61.03 g (97%) of crude oily product

Sources & evidence

ORD record
ord-7e5b32027fc04576a87889258ff3e4c5
Source dataset
uspto-grants-1997_08
Patent number
US05656617

Reaction notes

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