Triphenylphosphine → 16-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-benzyloxyhexyl)acetate

HRID 1289394

反応式

HRID 1289394 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:33][C:34]1[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:35]=1[C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]O)=[CH:43][CH:42]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:26]([O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]([O:18][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][O:47][C:44]1[CH:43]=[CH:42][C:41]([C:35]2[CH:36]=[CH:37][CH:38]=[C:39]([F:40])[C:34]=2[F:33])=[CH:46][CH:45]=1)=[O:17])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18920839HCID 18920839、化合物HCID 189208642,3-Difluoro-4'-(16-hydroxyhexadecyl)oxybiphenyl

生成物 1

HCID 1892085316-[2,3-Difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-benzyloxyhexyl)acetate収率 92.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

First, 3.4 g of 2,2-bis(6-benzyloxyhexyl)acetic acid, 3.3 g of 2,3-difluoro-4'-[16-hydroxyhexadecyl]oxybiphenyl, 2.3 g of triphenylphosphine, and 50 ml of tetrahyrofuran were placed in a 100 ml flask. Then, 1.5 g of diethyl azodicarboxylate was added dropwise to the reaction mixture at 5° C. Thereafter, the reaction mixture was allowed to warm to room temperature and stirred for 8 hours. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/9) to obtain 5.9 g of 16-[2,3-difluorobiphenyl-4'-yl]oxyhexadecyl 2,2-bis(6-benzyloxyhexyl)acetate (Y: 92.1%). The compound thus obtained had a purity of 98.3% by HPLC.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/9)

出典と根拠

ORDレコード
ord-66fc7f0f7c094088babdf26475eba60e
出典データセット
uspto-grants-1998_05
特許番号
US05750213

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