Water → HCID 54490045, compound

HRID 1974844Notes

Reaction equation

HRID 1974844 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 acetylchloride (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 ml) 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 acteate +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 ml) 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-50014de96d014b89b06dd24633c7aa46
Source dataset
uspto-grants-1994_02
Patent number
US05284837

Reaction notes

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